Perfume systems

ABSTRACT

The present application relates to perfume raw materials, perfume delivery systems and consumer products comprising such perfume raw materials and/or such perfume delivery systems, as well as processes for making and using such perfume raw materials, perfume delivery systems and consumer products. Such perfume raw materials and compositions, including the delivery systems, disclosed herein expand the perfume communities options as such perfume raw materials can provide variations on character and such compositions can provide desired odor profiles.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a Continuation of U.S. application Ser. No. 12/628,255, filed Dec. 1, 2009, which claims priority under 35 U.S.C. §119(e) to U.S. Provisional Application Ser. No. 61/118,720 filed Dec. 1, 2008.

FIELD OF INVENTION

The present application relates to perfume raw materials, perfume delivery systems and consumer products comprising such perfume raw materials and/or such perfume delivery systems, as well as processes for making and using such perfume raw materials, perfume delivery systems and consumer products.

BACKGROUND OF THE INVENTION

Consumer products may comprise one or more perfumes and/or perfume delivery systems that can provide a desired scent to such product and/or a situs that is contacted with such a product and/or mask an undesirable odor. While current perfumes and perfume delivery systems provide desirable odors, consumers continue to seek products that have scents that may be longer lasting and that are tailored to their individual desires (see for example USPA 2007/0275866 A1 and U.S. patent application Ser. No. 12/133,866)—unfortunately the pool of perfume raw materials and perfume delivery systems that is available is still too limited to completely meet the perfume community's needs. Thus, perfumers need an ever larger pool of perfume raw materials and perfume delivery systems.

Applicants believe that the perfume raw materials and compositions, including the delivery systems, disclosed herein expand the perfume community's options, as such perfume raw materials can provide variations on character and such compositions can provide desired odor profiles.

SUMMARY OF THE INVENTION

The present application relates to perfume raw materials, perfume systems and consumer products comprising such perfume raw materials and/or such perfume systems, as well as processes for making and using such perfume raw materials, perfume systems and consumer products.

DETAILED DESCRIPTION OF THE INVENTION Definitions

As used herein “consumer product” means baby care, beauty care, fabric & home care, family care, feminine care, health care, snack and/or beverage products or devices generally intended to be used or consumed in the form in which it is sold. Such products include but are not limited to diapers, bibs, wipes; products for and/or methods relating to treating hair (human, dog, and/or cat), including, bleaching, coloring, dyeing, conditioning, shampooing, styling; deodorants and antiperspirants; personal cleansing; cosmetics; skin care including application of creams, lotions, and other topically applied products for consumer use including fine fragrances; and shaving products, products for and/or methods relating to treating fabrics, hard surfaces and any other surfaces in the area of fabric and home care, including: air care including air fresheners and scent delivery systems, car care, dishwashing, fabric conditioning (including softening and/or freshing), laundry detergency, laundry and rinse additive and/or care, hard surface cleaning and/or treatment including floor and toilet bowl cleaners, and other cleaning for consumer or institutional use; products and/or methods relating to bath tissue, facial tissue, paper handkerchiefs, and/or paper towels; tampons, feminine napkins; products and/or methods relating to oral care including toothpastes, tooth gels, tooth rinses, denture adhesives, tooth whitening; over-the-counter health care including cough and cold remedies, pain relievers, RX pharmaceuticals, pet health and nutrition; processed food products intended primarily for consumption between customary meals or as a meal accompaniment (non-limiting examples include potato chips, tortilla chips, popcorn, pretzels, corn chips, cereal bars, vegetable chips or crisps, snack mixes, party mixes, multigrain chips, snack crackers, cheese snacks, pork rinds, corn snacks, pellet snacks, extruded snacks and bagel chips); and coffee.

As used herein, the term “cleaning and/or treatment composition” is a subset of consumer products that includes, unless otherwise indicated, beauty care, fabric & home care products. Such products include, but are not limited to, products for treating hair (human, dog, and/or cat), including, bleaching, coloring, dyeing, conditioning, shampooing, styling; deodorants and antiperspirants; personal cleansing; cosmetics; skin care including application of creams, lotions, and other topically applied products for consumer use including fine fragrances; and shaving products, products for treating fabrics, hard surfaces and any other surfaces in the area of fabric and home care, including: air care including air fresheners and scent delivery systems, car care, dishwashing, fabric conditioning (including softening and/or freshing), laundry detergency, laundry and rinse additive and/or care, hard surface cleaning and/or treatment including floor and toilet bowl cleaners, granular or powder-form all-purpose or “heavy-duty” washing agents, especially cleaning detergents; liquid, gel or paste-form all-purpose washing agents, especially the so-called heavy-duty liquid types; liquid fine-fabric detergents; hand dishwashing agents or light duty dishwashing agents, especially those of the high-foaming type; machine dishwashing agents, including the various tablet, granular, liquid and rinse-aid types for household and institutional use; liquid cleaning and disinfecting agents, including antibacterial hand-wash types, cleaning bars, mouthwashes, denture cleaners, dentifrice, car or carpet shampoos, bathroom cleaners including toilet bowl cleaners; hair shampoos and hair-rinses; shower gels, fine fragrances and foam baths and metal cleaners; as well as cleaning auxiliaries such as bleach additives and “stain-stick” or pre-treat types, substrate-laden products such as dryer added sheets, dry and wetted wipes and pads, nonwoven substrates, and sponges; as well as sprays and mists all for consumer or/and institutional use; and/or methods relating to oral care including toothpastes, tooth gels, tooth rinses, denture adhesives, tooth whitening.

As used herein, the term “fabric and/or hard surface cleaning and/or treatment composition” is a subset of cleaning and treatment compositions that includes, unless otherwise indicated, granular or powder-form all-purpose or “heavy-duty” washing agents, especially cleaning detergents; liquid, gel or paste-form all-purpose washing agents, especially the so-called heavy-duty liquid types; liquid fine-fabric detergents; hand dishwashing agents or light duty dishwashing agents, especially those of the high-foaming type; machine dishwashing agents, including the various tablet, granular, liquid and rinse-aid types for household and institutional use; liquid cleaning and disinfecting agents, including antibacterial hand-wash types, cleaning bars, car or carpet shampoos, bathroom cleaners including toilet bowl cleaners; and metal cleaners, fabric conditioning products including softening and/or freshing that may be in liquid, solid and/or dryer sheet form; as well as cleaning auxiliaries such as bleach additives and “stain-stick” or pre-treat types, substrate-laden products such as dryer added sheets, dry and wetted wipes and pads, nonwoven substrates, and sponges; as well as sprays and mists. All of such products which were applicable may be in standard, concentrated or even highly concentrated form even to the extent that such products may in certain aspect be non-aqueous.

As used herein, articles such as “a” and “an” when used in a claim, are understood to mean one or more of what is claimed or described.

As used herein, the terms “include”, “includes” and “including” are meant to be non-limiting.

As used herein, the term “solid” includes granular, powder, bar and tablet product forms.

As used herein, the term “fluid” includes liquid, gel, paste and gas product forms.

As used herein, the term “situs” includes paper products, fabrics, garments, hard surfaces, hair and skin.

Unless otherwise noted, all component or composition levels are in reference to the active portion of that component or composition, and are exclusive of impurities, for example, residual solvents or by-products, which may be present in commercially available sources of such components or compositions.

All percentages and ratios are calculated by weight unless otherwise indicated. All percentages and ratios are calculated based on the total composition unless otherwise indicated.

It should be understood that every maximum numerical limitation given throughout this specification includes every lower numerical limitation, as if such lower numerical limitations were expressly written herein. Every minimum numerical limitation given throughout this specification will include every higher numerical limitation, as if such higher numerical limitations were expressly written herein. Every numerical range given throughout this specification will include every narrower numerical range that falls within such broader numerical range, as if such narrower numerical ranges were all expressly written herein.

Suitable Perfume Raw Materials (Herein after “PRMs”)

Suitable PRMs include the PRMs listed in Table 1 below and stereoisomers thereof.

Chemical structure IUPAC Names Molecules Characteristics 1

2-cyclohexyl-1-phenylethanone Honey, pineapple, fruity, powerful (lingers) 2

2-methyl-4-phenyloctan-3-one Spicy, Celeery, green, basil 3

2,5-dimethyl-4-phenylhexan-3-one Honey, tea, aromatic, hay 4

2-methyl-4-phenylhexan-3-one Rose, friuty 5

2-cyclohexyl-1-(4- methylphenyl)ethanone 2-cyclohexyl-1-p-tolylethanone Floral, petrol/rubbery (styrene) 6

2-cycloheptyl-1-phenylethanone Almond, sweet, anisic, spicy 7

2-cyclopentyl-1-p-tolylethanone sweet, fruity (almond), floral (rose-geranium) 8

2-cyclopentyl-1-(4- ethylphenyl)ethanone musty, cheesy 9

2-cyclopentyl-1-(2,4,6- trimethylphenyl)ethanone clean nice character 10

2-cyclopentyl-1-phenylethanone cheesy, rose, floral, fruity ester, pineapple, acidic 11

3-cyclohexyl-1-phenylpropan-1-one Almond, floral, fruity (apple) 12

3-cyclohexyl-1-(4- ethylphenyl)propan-1-one Animalic, Matallic 13

3-cyclohexyl-1-(4- methylphenyl)propan-1-one 3-clohexyl-1-p-tolylpropan-1-one jasmin, ylang, animalic note 14

3-cyclohexyl-1-(2,4,6- trimethylphenyl)propan-1-one floral (muguet), green, fresh, sweet 15

4-(4-methylcyclohex-3-enyl)pentan- 2-ol Green, citrus, hay, cut grass 16

5-(4-methylcyclohex-3-enyl)hexan-3- ol Citrus, aldehydic, floral, muguet, unique in character 17

2-methyl-4-(4-methylcyclohex-3- enyl)pentan-2-ol Citrus, root, camphor 18

6-(4-methylcyclohex-3-enyl)hept-1- en-4-ol Geranium, floral 19

2-methyl-5-(4-methylcyclohex-3- enyl)hexan-3-ol Aldehydic, citrus, spicy 20

2,2-dimethyl-5-(4-methylcyclohex-3- enyl)hexan-3-ol Fruity (apple), diffusive, floral 21

2-(4-mcthylcyclohex-3-enyl)nonan-4- one Woody, cedar 22

4-(4-methylcyclohex-3-enyl)pentan- 2-one Fruity, Vertenex (woody), sour note, acrylic, very diffusive 23

5-(4-methylcyclohex-3-enyl)hexan-3- one Smokey, oily/buttery, ozonic, sour 24

2-methyl-5-(4-methylcyclohex-3- enyl)hexan-3-one Jasmin, lactonic, floral 25

2-(4-methylcyclohex-3-enyl)heptan- 4-one Floral, lactonic 26

6-(4-methylcyclohex-3-enyl)hept-1- en-4-one Fatty, aldehydic, frutene 27

2,2-dimethyl-5-(4-methylcyclohex-3- enyl)hexan-3-one Herbal, Tea, Terpentine 28

2,2-dimethyl-5-(4-methylcyclohex-3- enyl)hexan-3-yl acetate Floral, fruity 29

5-(4-methylcyclohex-3-enyl)hexan-3- yl acetate Fruity, Cassis 30

3-methyl-4-phenylbut-3-en-2-one floral (rose), citris, nitrilic, very diffusive 31

4-(4-methylphenyl)butan-2-one, 4-p-tolylbutan-2-one Floral, Sweet, Anisic 32

1-(3-methylphenyl)pent-1-en-3-one 1-m-tolylpent-1-en-3-one Chlorinated (bleach), honey, almond 33

3-methyl-4-(4-methylphenyl)but-3- en-2-one 3-methyl-4-p-tolylbut-3-en-2-one buttery 34

4-(2-methyl-3-oxobut-1- enyl)benzonitrile Sweet (honey), fruity 35

1-phenylhex-1-en-3-one Almond, sweet, candy 36

1-(2-methylphenyl)pent-1-en-3-one 1-o-tolylpent-1-en-3-one Floral, fruity, almond, saffron, anisic, diffusive 37

3-methyl-4-(2-methylphenyl)but-3- en-2-one 3-methyl-4-o-tolylbut-3-en-2-one rose, buttery, ionone 38

3-methyl-4-(3-methylphenyl)but-3- en-2-one 3-methyl-4-m-tolylbut-3-en-2-one nice, sweet, caramel, nutty 39

4-(4-methoxyphenyl)-3-methylbut-3- en-2-one sweet, burnt caramel 40

3-(4-methylbenzylidene)pentan-2-one floral, mimosa 41

1-(2-methylphenyl)hex-1-en-3-one 1-o-tolylhex-1-en-3-one Sweet, anisic, almond 42

1-(2,4,6-trimethylphenyl)hex-1-en-3- one Spicy, violet, rosy 43

1-(2,4,6-trimethylphenyl)pent-1-en-3- one Saffron, floral, animalic 44

3-methyl-4-(2,4,6- trimethylphenyl)but-3-en-2-one Aromatic, herbal, anisic 45

1-(2,6-dimethylphenyl)hex-1-en-3- one Floral, violet 46

1-(2,6-dimethylphenyl)pent-1-en-3- one Spicy, floral, saffron 47

1-(3-methylphenyl)hex-1-en-3-one 1-m-tolylhex-1-en-3-one Sweet, fruity, almond 48

1-cyclohexyl-2-phenylpropan-1-one Glue, rose, fruity 49

2,2,4,7-tetramethyloct-6-en-3-one citrus, herbal (lavender ketone hint) 50

2,4(R,S),7-trimethyloct-6-en-3-one grapefruit, green 51

2,2,4,4,7-pentamethyloct-6-en-3-one lime, spicy, herbal, diffusive, citrus, citronella 52

Ethyl 2(R,S),5-dimethyl-2- (pivaloyl)hex-4-enoate 53

2,2,7-Trimethyl-4-(3-methylbut-2- enyl)oct-6-en-3-one 54

1-(1-(3-methylbut-2- enyl)cyclohexyl)ethanone rose, citrus, grapefruit 55

1-(1-(3-methylbut-2- enyl)cyclohexyl)propan-1-one chemical 56

2-methyl-1-(1-(3-methylbut-2- enyl)cyclohexyl)propan-1-one weak (gun powder) 57

4,4,7-trimethyloct-6-en-3-one rosey-geranium, grapefruit 58

1-(1-(3-methylbut-2- enyl)cyclopentyl)ethanone Grapefruit 59

1-(1-(3-methylbut-2- enyl)cyclopentyl)propan-1-one rose, fruity 60

3,6-dimethyl-3-(3-methylbut-2- enyl)hept-5-en-2-one Rose 61

3(R,S),6-dimethylhept-5-en-2-one 62

1-(1-(3-hydroxy-3- methylbutyl)cyclohexyl)-2- methylpropan-1-one chemical, acid 63

5-methyl-2(R,S)-(prop-1-en-2-yl)- hex-4-enoic acid 64

2-methyl-1-(1-(3-methylbut-2- enyl)cyclopentyl)propan-1-one fruity, chemical 65

4,7-dimethyl-4-(3-methylbut-2- enyl)oct-6-en-3-one Rose 66

2,4,7-trimethyl-4-(3-methylbut-2- enyl)oct-6-en-3-one Bleach 67

3(R,S),5,5,8-tetramethylnon-7-en-4- one fruity, grapefruit 68

1-(1-(3-methylbut-2- enyl)cyclopropyl)ethanone Fruity, ethereal 69

2-methyl-1-(1-(3-(R,S)-methylbut-2- enyl)cyclopropyl)butan-1-one fruity (grapefruit-plum) 70

2-methyl-1-(1-(3-methylbut-2- enyl)cyclopropyl)propan-1-one citrus, grapefruit 71

1-(1-(3-methylbut-2- enyl)cyclopropyl)pentan-1-one fruity-spicy (garpaccio)- metallic 72

9-methyldec-8-en-3 one waxy, fruity, clean (→green, violet) 73

2,5-dimethyl-2-(3-methylbut-2- enyl)hex-4-enenitrile geranium, rose, terpenic 74

1-(3-methylbut-2- enyl)cyclopentanecarbonitrile spicy, nutty, rubbery 75

1-(3-methylbut-2- enyl)cyclohexanecarbonitrile herbal-aromatic, floral-green 76

1-(3-methylbut-2- enyl)cyclopropanecarbonitrile minty, nutty 77

1-(3-methylbut-2- enyl)cyclobutanecarbonitrile celery, diffusive 78

2-methyl-1-(1-(3-(R,S)-methylbut-2- enyl)cyclobutyl)butan-1-one fruity, herbal (menthol) 79

1-(1-(3-methylbut-2- enyl)cyclobutyl)ethanone citrus, aromatic, diffusive 80

2-(R,S)-methyl-1-(1- phenylcyclopropyl)butan-1-one woody, earthy 81

1-(1-(3-methylbut-2- enyl)cyclobutyl)pentan-1-one Spearmint 82

2-methyl-1-(1-(3-methylbut-2- enyl)cyclobutyl)propan-1-one pine, terpenic 83

1-(1-phenylcyclopropyl)propan-1-one woody, earthy, orange (over- ripe), 84

2-methyl-1-(1- phenylcyclopropyl)propan-1-one woody, gunpowder, (fougere) 85

1-(1-(3-methylbut-2- enyl)cyclopropyl)propan-1-one terpenic, herbal 86

3-methyl-1-(1-(3-methylbut-2- enyl)cyclopropyl)butan-1-one metallic, fruity 87

1-(1-p-tolylcyclopropyl)propan-1-one oily, solventy, nutty 88

2-(R,S)-methyl-1-(1-p- tolylcyclopropyl)butan-1-one woody, weak 89

1-(1-(3-methylbut-2-enyl)-3- methylenecyclobutyl)ethanone herbal (edible-oxo) 90

1-(1-phenylcyclobutyl)pentan-1-one styrene, oily 91

2,2,5-trimethylhex-4-enenitrile earthy, ozonic, vetyver 92

6,6,9-trimethyldec-8-en-5-one floral, intense 93

2,5,5,8-tetramethylnon-7-en-4-one floral, valerianic 94

1-(1-(3-methylbut-2- enyl)cyclopcntyl)pentan-1-one floral, valerianic 95

3-methyl-1-(1-(3-methylbut-2- enyl)cyclopentyl)butan-1-one floral, valerianic 96

2,2-dimethyl-1-(1-(3-methylbut-2- enyl)cyclopropyl)propan-1-one citrus, fresh, diffusive 97

2-methyl-1-(1-p- tolylcyclopropyl)propan-1-one almond, chemical 98

1-(1-((E)-3,7-dimethylocta-2,6- dienyl)cyclopropyl)ethanone Spicy 99

2-methyl-1-(1-((E)-3,7-dimethylocta- 2,6-dienyl)cyclopropyl)butan-1-one herbal, green, fruity (natural) 100

2,4-dimethyl-2-m-tolylpentan-3-one intense, tobacco (sweet), earthy 101

2-methyl-2-m-tolylpropanetrile intense, root, vetyver 102

3-methyl-3-m-tolylbutan-2-one burnt, caramelized 103

2-methyl-2-m-tolylpentan-3-one diffusive, orange flower 104

1-(1-p-tolylcyclopentyl)ethanone spicy, vegetable 105

7-methyl-1-phenyloct-6-en-1-one truffle, oriental bouillon 106

2,2-dimethyl-3-o-tolylpropanenitrile saffras, earthy, woody 107

3,3-dimethyl-4-o-tolylbutan-2-one Cedarwood 108

2,2-dimethyl-1-o-tolylpentan-3-one woody, citrus, medicinal 109

o-methyl- benzylcyclopropanecarbonitrile woody, spicy, chemical 110

2,2,4-trimethyl-1-o-tolylhexan-3-one floral, terpineol, camomile, green 111

1-(1-(2-methylbenzyl)- cyclopropyl)propanone rose, violet, woody 112

1-(1-(2- methylbenzyl)cyclopropyl)ethanone leathery, powdery 113

2-(R,S)-methyl-1-(1-(2- methylbenzyl)cyclopropyl)butan-1- one fruity, tutti-frutti, citrus 114

2-methyl-1-(1-(2- methylbenzyl)cyclopropyl)propan-1- one citrus, fruity (apple) 115

2,2,5-trimethyl-1-phenylhexan-3-one intense, woody, celery, anima 116

2-(1-(3-methylbut-2- enyl)cyclopropyl)propan-2-ol intense, floral, lilac, terpineol 117

1-(1-(3-methylbut-2- enyl)cyclopbutyl)propan-1-one woody, camphor, costus 118

2-(R,S)-(1-(3-methylbut-2- enyl)cyclobutyl)butan-2-ol citrus, herbal, bleach 119

1-(R,S)-(1-(3-methylbut-2- enyl)cyclobutyl)propan-1-ol Weak 120

9-methyldec-1,8-dien-3-one diffusive, very intense, metallic, smoky (gun powder) 121

2,2-dimethyl-3-(R,S)- phenylbutanenitrile tobacco, floral (violet) 122

4,4-dimethyl-5-(R,S)-phenylhexan-3- one herbal (green, chamomile) 123

1-cyclopentyl-7-methyloct-6-en-1- one very intense, nutty, spicy, green (galbanum) 124

2,2-dimethyl-3-p-tolylpropanenitrile chervil, fennel, celery, mint 125

3-(4-methoxy-3-methylphenyl)-3- methylbutan-2-one leatherym, quinone 126

2,2,4-(R,S)-trimethyl-1-p-tolylhexan- 3-one weak, chocolate, nutty 127

3,3-dimethyl-4-(R,S)-phenylpentan- 2-one diffusive, herbal, citrus 128

2,2-dimethyl-1-p-tolylpentan-3-one fennel, herbal 129

3-(R,S)-(1-(3-methylbut-2- enyl)cyclobutyl)heptan-3-ol citrus, amber 130

3-cyclohexyl-2,2- dimethylpropanenitrile intense, mint, marine, spicy 131

1-cyclohexyl-2,2,4-trimethylpentan- 3-one Peppery 132

1-(R,S)-(1-phenylethyl)- cyclobutanecarbonitrile chemical, solventy 133

1-(1-(R,S)-(1-phenylethyl)- cyclobutyl)ethanone chemical, solventy, animalic 134

2-methyl-1-(1-(R,S)-(1- phenylethyl)cyclobutyl)propan-1-one chemical, orange flower 135

2-methyl-1-(R,S)-(1-(1-(R,s)- phenylethyl)cyclobutyl)propan-1-ol Chemical 136

1-(1-(R,S)- phenylethyl)cyclopropanecarbonitrile Petrol 137

1-(1-(1-(R,S)- phenylethyl)cyclopropyl)ethanone green, floral, chemical 138

2,2-dimethyl-3-m-tolylpropanenitrile orange crystals 139

3-(4-tert-butylphcnyl)-2,2- dimethylpropanenitrile woody, floral 140

1-(1-phenylcyclopropyl)but-3-en-1- one fruity (berries), green 141

1-(1-phenylcyclopropyl)but-3-en-1- (R,s)-ol floral, chemical 142

4-(4-tert-butylphenyl)-3,3- dimethylbutan-2-one Sulphuric 143

2,2-dimethyl-4-phenylbutanenitrile Chemical 144

11-methyldodec-10-en-5-one Seafood 145

2,9-dimethyldec-8-en-3-one intense, fruity, oily, clean 146

2,10-dimethylundec-9-en-4-one intense, waxy, aldehydic, floral, fruity (melon) 147

2,2,9-trimethyldec-8-en-3-one intense, woody, waxy 148

2,2,3-(R,S),7-tetramethyloct-6- enenitrile citrus, waxy, bleach 149

4,4,5-(R,S),9-tetramethyldec-8-en-3- one intense, floral, waxy 150

6,6,7-(R,S),11-tetramethyldodec-10- en-5-one celery, green, floral 151

3,3-dimethyl-5-phenylpentan-s-one glue, sweet 152

2-((R,S)-cyclohex-2-enyl)-2- methylpropanenitrile intense, woody, camphoraceous 153

2-((R,S)-cyclohex-2-enyl)-2,5- dimethylhexan-3-one citrus, herbal 154

3,3-dimethyl-1-phenyloctan-4-one Chemical 155

2-((R,S)-cyclohex-2-enyl)-2- methylpentan-3-one intense, fruity, floral, woody, spicy 156

4,4-dimethyl-6-phenylhexan-3-one Floral, woody 157

2,2-dimethyl-5-phenylpentanenitrile citrus, nitrile, chemical, clean 158

2,2-dimethylhept-6-enenitrile intense, floral, celery 159

6,6-dimethylundec-10-en-5-one Waxy, clean 160

3,3-dimethyl-6-phenylhexan-2-one citrus, herbal 161

2,2-dimethyl-4-((1R,5S)-6,6- dimethylbicyclo[3.1.1]hept-2-en-2- yl)butanenitrile floral, spicy (peppery), woody

The PRMs disclosed in Table 1 above may provide one or more of the following benefits at a level that Applicants believe is unexpected in view of PRMs in general: neat product odor; wet fabric odor when applied to a fabric; dry fabric odor when applied to a fabric; reduced leakage from an encapsulate, including an encapsulate such as a perfume microcapsule; increased head space versus neat oil in certain perfume delivery technologies; odor when used in a matrix perfume delivery that is applied to a package; neat product odor when applied to a cleaning and/or treatment composition; fine fragrance composition odor when used in a fine fragrance; dry hair odor when a composition comprising such a PRM is applied to hair; PRM bloom from a solution comprising such a PRM and new PRM character when applied to a situs. Confirmation of such benefits can be obtained by applying standard test methodologies.

The PRMs and stereoisomers of such PRMs (also known as molecules in the examples of the present specification) disclosed in Table 1 above can be made in accordance with the respective teachings found, for example in the examples of the present specification.

In one aspect, a PRM having the structure of Table 1 PRM 16, 20, 27, 28, 118, 123 and 140 are disclosed.

In one aspect, the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use, as defined by the present specification, in consumer products at levels, based on total consumer product weight of from about 0.0001% to about 25%, from about 0.0005% to about 10%, from about 0.001% to about 5%, from about 0.005% to about 2.5%, or even from 0.01% to about 1%. Such PRMs and stereoisomers thereof may be used in combination in the aforementioned consumer product. In one aspect, a consumer product that may comprise one or more PRMs selected from Table 1 PRMs 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 118, 123, 140 and stereoisomers of such PRMs is disclosed.

In one aspect, the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use, as defined by the present specification, in cleaning and/or treatment composition at levels, based on total cleaning and treatment products weight of from about 0.0001% to about 25%, from about 0.0005% to about 10%, from about 0.001% to about 5%, from about 0.005% to about 2.5%, or even from 0.01% to about 1%. Such PRMs and stereoisomers thereof may be used in combination in the aforementioned cleaning and/ treatment compositions. In one aspect, a cleaning and/or treatment composition that may comprise one or more PRMs selected from Table 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 77, 100, 101, 107, 108, 110, 117, 118, 123, 127, 140 and stereoisomers of such PRMs is disclosed.

In one aspect, the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use, as defined by the present specification, in fabric and/or hard surface cleaning and/or treatment compositions at levels, based on total fabric and/or hard surface cleaning and/or treatment composition weight of from about 0.00001% to about 25%, from 0.00005% to about 10%, from 0.0001% to about 5%, from 0.0005% to about 1.0%, or even from 0.001% to about 0.5%. Such PRMs and stereoisomers thereof may be used in combination in the aforementioned fabric and/or hard surface cleaning and/or treatment compositions. In one aspect, a fabric and/or hard surface cleaning and/or treatment composition that may comprise one or more PRMs selected from Table 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 33, 34, 35, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 74, 75, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 117, 118, 119, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161 and stereoisomers of such PRMs is disclosed.

In one aspect, a detergent that may comprise the same level of the PRMs as disclosed for the aforementioned fabric and hard surface cleaning and/or treatment compositions is disclosed. In one aspect, a detergent that may comprise one or more PRMs selected from Table 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 33, 34, 35, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 74, 75, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 117, 118, 119, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161 and stereoisomers of such PRMs is disclosed.

In one aspect, the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use, in highly compacted consumer products, including highly compacted fabric and hard surface cleaning and/or treatment compositions, for example highly compacted detergents that may be solids or fluids, at levels, based on total composition weight, of from about 0.00001% to about 25%, from 0.00005% to about 10%, from 0.0001% to about 5%, from 0.0005% to about 1.0%, or even from 0.001% to about 0.5%. Such PRMs and stereoisomers thereof may be used in combination in the aforementioned highly compacted detergent compositions. Such highly compact detergents typically comprise a higher than normal percentage of active ingredients. In one aspect, a highly compacted detergent that may comprise one or more PRMs selected from Table 1 PRMs and stereoisomers of such PRMs is disclosed. In another aspect, highly compacted a detergent that may comprise one or more PRMs selected from Table 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161 and stereoisomers of such PRMs is disclosed.

Perfume Delivery Systems

Certain perfume delivery systems, methods of making certain perfume delivery systems and the uses of such perfume delivery systems are disclosed in USPA 2007/0275866 A1. Such perfume delivery systems include:

I. Polymer Assisted Delivery (PAD): This perfume delivery technology uses polymeric materials to deliver perfume materials. Classical coacervation, water soluble or partly soluble to insoluble charged or neutral polymers, liquid crystals, hot melts, hydrogels, perfumed plastics, microcapsules, nano- and micro-latexes, polymeric film formers, and polymeric absorbents, polymeric adsorbents, etc. are some examples. PAD includes but is not limited to:

-   -   a.) Matrix Systems: The fragrance is dissolved or dispersed in a         polymer matrix or particle. Perfumes, for example, may be 1)         dispersed into the polymer prior to formulating into the product         or 2) added separately from the polymer during or after         formulation of the product. Diffusion of perfume from the         polymer is a common trigger that allows or increases the rate of         perfume release from a polymeric matrix system that is deposited         or applied to the desired surface (situs), although many other         triggers are know that may control perfume release. Absorption         and/or adsorption into or onto polymeric particles, films,         solutions, and the like are aspects of this technology. Nano- or         micro-particles composed of organic materials (e.g., latexes)         are examples. Suitable particles include a wide range of         materials including, but not limited to polyacetal,         polyacrylate, polyacrylic, polyacrylonitrile, polyamide,         polyaryletherketone, polybutadiene, polybutylene, polybutylene         terephthalate, polychloroprene, poly ethylene, polyethylene         terephthalate, polycyclohexylene dimethylene terephthalate,         polycarbonate, polychloroprene, polyhydroxyalkanoate,         polyketone, polyester, polyethylene, polyetherimide,         polyethersulfone, polyethylenechlorinates, polyimide,         polyisoprene, polylactic acid, polymethylpentene, polyphenylene         oxide, polyphenylene sulfide, polyphthalamide, polypropylene,         polystyrene, polysulfone, polyvinyl acetate, polyvinyl chloride,         as well as polymers or copolymers based on         acrylonitrile-butadiene, cellulose acetate, ethylene-vinyl         acetate, ethylene vinyl alcohol, styrene-butadiene, vinyl         acetate-ethylene, and mixtures thereof.         -   “Standard” systems refer to those that are “pre-loaded” with             the intent of keeping the pre-loaded perfume associated with             the polymer until the moment or moments of perfume release.             Such polymers may also suppress the neat product odor and             provide a bloom and/or longevity benefit depending on the             rate of perfume release. One challenge with such systems is             to achieve the ideal balance between 1) in-product stability             (keeping perfume inside carrier until you need it) and 2)             timely release (during use or from dry situs). Achieving             such stability is particularly important during in-product             storage and product aging. This challenge is particularly             apparent for aqueous-based, surfactant-containing products,             such as heavy duty liquid laundry detergents. Many             “Standard” matrix systems available effectively become             “Equilibrium” systems when formulated into aqueous-based             products. One may select an “Equilibrium” system or a             Reservoir system, which has acceptable in-product diffusion             stability and available triggers for release (e.g.,             friction). “Equilibrium” systems are those in which the             perfume and polymer may be added separately to the product,             and the equilibrium interaction between perfume and polymer             leads to a benefit at one or more consumer touch points             (versus a free perfume control that has no polymer-assisted             delivery technology). The polymer may also be pre-loaded             with perfume; however, part or all of the perfume may             diffuse during in-product storage reaching an equilibrium             that includes having desired perfume raw materials (PRMs)             associated with the polymer. The polymer then carries the             perfume to the surface, and release is typically via perfume             diffusion. The use of such equilibrium system polymers has             the potential to decrease the neat product odor intensity of             the neat product (usually more so in the case of pre-loaded             standard system). Deposition of such polymers may serve to             “flatten” the release profile and provide increased             longevity. As indicated above, such longevity would be             achieved by suppressing the initial intensity and may enable             the formulator to use more high impact or low odor detection             threshold (ODT) or low Kovats Index (KI) PRMs to achieve             FMOT benefits without initial intensity that is too strong             or distorted. It is important that perfume release occurs             within the time frame of the application to impact the             desired consumer touch point or touch points. Suitable             micro-particles and micro-latexes as well as methods of             making same may be found in USPA 2005/0003980 A1. Matrix             systems also include hot melt adhesives and perfume             plastics. In addition, hydrophobically modified             polysaccharides may be formulated into the perfumed product             to increase perfume deposition and/or modify perfume             release. All such matrix systems, including for example             polysaccarides and nanolatexes may be combined with other             PDTs, including other PAD systems such as PAD reservoir             systems in the form of a perfume microcapsule (PMC). Polymer             Assisted Delivery (PAD) matrix systems may include those             described in the following references: US Patent             Applications 2004/0110648 A1; 2004/0092414 A1; 2004/0091445             A1 and 2004/0087476 A1; and U.S. Pat. Nos. 6,531,444;             6,024,943; 6,042,792; 6,051,540; 4,540,721 and 4,973,422.         -   Silicones are also examples of polymers that may be used as             PDT, and can provide perfume benefits in a manner similar to             the polymer-assisted delivery “matrix system”. Such a PDT is             referred to as silicone-assisted delivery (SAD). One may             pre-load silicones with perfume, or use them as an             equilibrium system as described for PAD. Suitable silicones             as well as making same may be found in WO 2005/102261; USPA             20050124530A1; USPA 20050143282A1; and WO 2003/015736.             Functionalized silicones may also be used as described in             USPA 2006/003913 A1. Examples of silicones include             polydimethylsiloxane and polyalkyldimethylsiloxanes. Other             examples include those with amine functionality, which may             be used to provide benefits associated with amine-assisted             delivery (AAD) and/or polymer-assisted delivery (PAD) and/or             amine-reaction products (ARP). Other such examples may be             found in U.S. Pat. No. 4,911,852; USPA 2004/0058845 A1; USPA             2004/0092425 A1 and USPA 2005/0003980 A1.     -   b.) Reservoir Systems: Reservoir systems are also known as a         core-shell type technology, or one in which the fragrance is         surrounded by a perfume release controlling membrane, which may         serve as a protective shell. The material inside the         microcapsule is referred to as the core, internal phase, or         fill, whereas the wall is sometimes called a shell, coating, or         membrane. Microparticles or pressure sensitive capsules or         microcapsules are examples of this technology. Microcapsules of         the current invention are formed by a variety of procedures that         include, but are not limited to, coating, extrusion,         spray-drying, interfacial, in-situ and matrix polymerization.         The possible shell materials vary widely in their stability         toward water. Among the most stable are polyoxymethyleneurea         (PMU)-based materials, which may hold certain PRMs for even long         periods of time in aqueous solution (or product). Such systems         include but are not limited to urea-formaldehyde and/or         melamine-formaldehyde. Gelatin-based microcapsules may be         prepared so that they dissolve quickly or slowly in water,         depending for example on the degree of cross-linking. Many other         capsule wall materials are available and vary in the degree of         perfume diffusion stability observed. Without wishing to be         bound by theory, the rate of release of perfume from a capsule,         for example, once deposited on a surface is typically in reverse         order of in-product perfume diffusion stability. As such,         urea-formaldehyde and melamine-formaldehyde microcapsules for         example, typically require a release mechanism other than, or in         addition to, diffusion for release, such as mechanical force         (e.g., friction, pressure, shear stress) that serves to break         the capsule and increase the rate of perfume (fragrance)         release. Other triggers include melting, dissolution, hydrolysis         or other chemical reaction, electromagnetic radiation, and the         like. The use of pre-loaded microcapsules requires the proper         ratio of in-product stability and in-use and/or on-surface         (on-situs) release, as well as proper selection of PRMs.         Microcapsules that are based on urea-formaldehyde and/or         melamine-formaldehyde are relatively stable, especially in near         neutral aqueous-based solutions. These materials may require a         friction trigger which may not be applicable to all product         applications. Other microcapsule materials (e.g., gelatin) may         be unstable in aqueous-based products and may even provide         reduced benefit (versus free perfume control) when in-product         aged. Scratch and sniff technologies are yet another example of         PAD. Perfume microcapsules (PMC) may include those described in         the following references: US Patent Applications: 2003/0125222         A1; 2003/215417 A1; 2003/216488 A1; 2003/158344 A1; 2003/165692         A1; 2004/071742 A1; 2004/071746 A1; 2004/072719 A1; 2004/072720         A1; 2006/0039934 A1; 2003/203829 A1; 2003/195133 A1; 2004/087477         A1; 2004/0106536 A1; and U.S. Pat. Nos. 6,645,479 B1; 6,200,949         B1; 4,882,220; 4,917,920; 4,514,461; 6,106,875 and 4,234,627,         3,594,328 and U.S. RE 32713.         II. Molecule-Assisted Delivery (MAD): Non-polymer materials or         molecules may also serve to improve the delivery of perfume.         Without wishing to be bound by theory, perfume may         non-covalently interact with organic materials, resulting in         altered deposition and/or release. Non-limiting examples of such         organic materials include but are not limited to hydrophobic         materials such as organic oils, waxes, mineral oils, petrolatum,         fatty acids or esters, sugars, surfactants, liposomes and even         other perfume raw material (perfume oils), as well as natural         oils, including body and/or other soils. Perfume fixatives are         yet another example. In one aspect, non-polymeric materials or         molecules have a CLogP greater than about 2. Molecule-Assisted         Delivery (MAD) may also include those described in U.S. Pat. No.         7,119,060 and U.S. Pat. No. 5,506,201.         III. Fiber-Assisted Delivery (FAD): The choice or use of a situs         itself may serve to improve the delivery of perfume. In fact,         the situs itself may be a perfume delivery technology. For         example, different fabric types such as cotton or polyester will         have different properties with respect to ability to attract         and/or retain and/or release perfume. The amount of perfume         deposited on or in fibers may be altered by the choice of fiber,         and also by the history or treatment of the fiber, as well as by         any fiber coatings or treatments. Fibers may be woven and         non-woven as well as natural or synthetic. Natural fibers         include those produced by plants, animals, and geological         processes, and include but are not limited to cellulose         materials such as cotton, linen, hemp jute, flax, ramie, and         sisal, and fibers used to manufacture paper and cloth.         Fiber-Assisted Delivery may consist of the use of wood fiber,         such as thermomechanical pulp and bleached or unbleached kraft         or sulfite pulps. Animal fibers consist largely of particular         proteins, such as silk, sinew, catgut and hair (including wool).         Polymer fibers based on synthetic chemicals include but are not         limited to polyamide nylon, PET or PBT polyester,         phenol-formaldehyde (PF), polyvinyl alcohol fiber (PVOH),         polyvinyl chloride fiber (PVC), polyolefins (PP and PE), and         acrylic polymers. All such fibers may be pre-loaded with a         perfume, and then added to a product that may or may not contain         free perfume and/or one or more perfume delivery technologies.         In one aspect, the fibers may be added to a product prior to         being loaded with a perfume, and then loaded with a perfume by         adding a perfume that may diffuse into the fiber, to the         product. Without wishing to be bound by theory, the perfume may         absorb onto or be adsorbed into the fiber, for example, during         product storage, and then be released at one or more moments of         truth or consumer touch points.         IV. Amine Assisted Delivery (AAD): The amine-assisted delivery         technology approach utilizes materials that contain an amine         group to increase perfume deposition or modify perfume release         during product use. There is no requirement in this approach to         pre-complex or pre-react the perfume raw material(s) and amine         prior to addition to the product. In one aspect,         amine-containing AAD materials suitable for use herein may be         non-aromatic; for example, polyalkylimine, such as         polyethyleneimine (PEI), or polyvinylamine (PVAm), or aromatic,         for example, anthranilates. Such materials may also be polymeric         or non-polymeric. In one aspect, such materials contain at least         one primary amine. This technology will allow increased         longevity and controlled release also of low ODT perfume notes         (e.g., aldehydes, ketones, enones) via amine functionality, and         delivery of other PRMs, without being bound by theory, via         polymer-assisted delivery for polymeric amines. Without         technology, volatile top notes can be lost too quickly, leaving         a higher ratio of middle and base notes to top notes. The use of         a polymeric amine allows higher levels of top notes and other         PRMS to be used to obtain freshness longevity without causing         neat product odor to be more intense than desired, or allows top         notes and other PRMs to be used more efficiently. In one aspect,         AAD systems are effective at delivering PRMs at pH greater than         about neutral. Without wishing to be bound by theory, conditions         in which more of the amines of the AAD system are deprotonated         may result in an increased affinity of the deprotonated amines         for PRMs such as aldehydes and ketones, including unsaturated         ketones and enones such as damascone. In another aspect,         polymeric amines are effective at delivering PRMs at pH less         than about neutral. Without wishing to be bound by theory,         conditions in which more of the amines of the AAD system are         protonated may result in a decreased affinity of the protonated         amines for PRMs such as aldehydes and ketones, and a strong         affinity of the polymer framework for a broad range of PRMs. In         such an aspect, polymer-assisted delivery may be delivering more         of the perfume benefit; such systems are a subspecies of AAD and         may be referred to as Amine-Polymer-Assisted Delivery or APAD.         In some cases when the APAD is employed in a composition that         has a pH of less than seven, such APAD systems may also be         considered Polymer-Assisted Delivery (PAD). In yet another         aspect, AAD and PAD systems may interact with other materials,         such as anionic surfactants or polymers to form coacervate         and/or coacervates-like systems. In another aspect, a material         that contains a heteroatom other than nitrogen, for example         sulfur, phosphorus or selenium, may be used as an alternative to         amine compounds. In yet another aspect, the aforementioned         alternative compounds can be used in combination with amine         compounds. In yet another aspect, a single molecule may comprise         an amine moiety and one or more of the alternative heteroatom         moieties, for example, thiols, phosphines and selenols. Suitable         AAD systems as well as methods of making same may be found in US         Patent Applications 2005/0003980 A1; 2003/0199422 A1;         2003/0036489 A1; 2004/0220074 A1 and U.S. Pat. No. 6,103,678.         V. Cyclodextrin Delivery System (CD): This technology approach         uses a cyclic oligosaccharide or cyclodextrin to improve the         delivery of perfume. Typically a perfume and cyclodextrin (CD)         complex is formed. Such complexes may be preformed, formed         in-situ, or formed on or in the situs. Without wishing to be         bound by theory, loss of water may serve to shift the         equilibrium toward the CD-Perfume complex, especially if other         adjunct ingredients (e.g., surfactant) are not present at high         concentration to compete with the perfume for the cyclodextrin         cavity. A bloom benefit may be achieved if water exposure or an         increase in moisture content occurs at a later time point. In         addition, cyclodextrin allows the perfume formulator increased         flexibility in selection of PRMs. Cyclodextrin may be pre-loaded         with perfume or added separately from perfume to obtain the         desired perfume stability, deposition or release benefit.         Suitable CDs as well as methods of making same may be found in         USPA 2005/0003980 A1 and 2006/0263313 A1 and U.S. Pat. Nos.         5,552,378; 3,812,011; 4,317,881; 4,418,144 and 4,378,923.         VI. Starch Encapsulated Accord (SEA): The use of a starch         encapsulated accord (SEA) technology allows one to modify the         properties of the perfume, for example, by converting a liquid         perfume into a solid by adding ingredients such as starch. The         benefit includes increased perfume retention during product         storage, especially under non-aqueous conditions. Upon exposure         to moisture, a perfume bloom may be triggered. Benefits at other         moments of truth may also be achieved because the starch allows         the product formulator to select PRMs or PRM concentrations that         normally cannot be used without the presence of SEA. Another         technology example includes the use of other organic and         inorganic materials, such as silica to convert perfume from         liquid to solid. Suitable SEAs as well as methods of making same         may be found in USPA 2005/0003980 A1 and U.S. Pat. No. 6,458,754         B1.         VII. Inorganic Carrier Delivery System (ZIC): This technology         relates to the use of porous zeolites or other inorganic         materials to deliver perfumes. Perfume-loaded zeolite may be         used with or without adjunct ingredients used for example to         coat the perfume-loaded zeolite (PLZ) to change its perfume         release properties during product storage or during use or from         the dry situs. Suitable zeolite and inorganic carriers as well         as methods of making same may be found in USPA 2005/0003980 A1         and U.S. Pat. Nos. 5,858,959; 6,245,732 B1; 6,048,830 and         4,539,135. Silica is another form of ZIC. Another example of a         suitable inorganic carrier includes inorganic tubules, where the         perfume or other active material is contained within the lumen         of the nano- or micro-tubules. In one aspect, the perfume-loaded         inorganic tubule (or Perfume-Loaded Tubule or PLT) is a mineral         nano- or micro-tubule, such as halloysite or mixtures of         halloysite with other inorganic materials, including other         clays. The PLT technology may also comprise additional         ingredients on the inside and/or outside of the tubule for the         purpose of improving in-product diffusion stability, deposition         on the desired situs or for controlling the release rate of the         loaded perfume. Monomeric and/or polymeric materials, including         starch encapsulation, may be used to coat, plug, cap, or         otherwise encapsulate the PLT. Suitable PLT systems as well as         methods of making same may be found in U.S. Pat. No. 5,651,976.         VIII. Pro-Perfume (PP): This technology refers to perfume         technologies that result from the reaction of perfume materials         with other substrates or chemicals to form materials that have a         covalent bond between one or more PRMs and one or more carriers.         The PRM is converted into a new material called a pro-PRM (i.e.,         pro-perfume), which then may release the original PRM upon         exposure to a trigger such as water or light. Pro-perfumes may         provide enhanced perfume delivery properties such as increased         perfume deposition, longevity, stability, retention, and the         like. Pro-perfumes include those that are monomeric         (non-polymeric) or polymeric, and may be pre-formed or may be         formed in-situ under equilibrium conditions, such as those that         may be present during in-product storage or on the wet or dry         situs. Nonlimiting examples of pro-perfumes include Michael         adducts (e.g., beta-amino ketones), aromatic or non-aromatic         imines (Schiff bases), oxazolidines, beta-keto esters, and         orthoesters. Another aspect includes compounds comprising one or         more beta-oxy or beta-thio carbonyl moieties capable of         releasing a PRM, for example, an alpha, beta-unsaturated ketone,         aldehyde or carboxylic ester. The typical trigger for perfume         release is exposure to water; although other triggers may         include enzymes, heat, light, pH change, autoxidation, a shift         of equilibrium, change in concentration or ionic strength and         others. For aqueous-based products, light-triggered pro-perfumes         are particularly suited. Such photo-pro-perfumes (PPPs) include         but are not limited to those that release coumarin derivatives         and perfumes and/or pro-perfumes upon being triggered. The         released pro-perfume may release one or more PRMs by means of         any of the above mentioned triggers. In one aspect, the         photo-pro-perfume releases a nitrogen-based pro-perfume when         exposed to a light and/or moisture trigger. In another aspect,         the nitrogen-based pro-perfume, released from the         photo-pro-perfume, releases one or more PRMs selected, for         example, from aldehydes, ketones (including enones) and         alcohols. In still another aspect, the PPP releases a dihydroxy         coumarin derivative. The light-triggered pro-perfume may also be         an ester that releases a coumarin derivative and a perfume         alcohol. In one aspect the pro-perfume is a dimethoxybenzoin         derivative as described in USPA 2006/0020459 A1. In another         aspect the pro-perfume is a 3′,5′-dimethoxybenzoin (DMB)         derivative that releases an alcohol upon exposure to         electromagnetic radiation. In yet another aspect, the         pro-perfume releases one or more low ODT PRMs, including         tertiary alcohols such as linalool, tetrahydrolinalool, or         dihydromyrcenol. Suitable pro-perfumes and methods of making         same can be found in U.S. Pat. Nos. 7,018,978 B2; 6,987,084 B2;         6,956,013 B2; 6,861,402 B1; 6,544,945 B1; 6,093,691; 6,277,796         B1; 6,165,953; 6,316,397 B1; 6,437,150 B1; 6,479,682 B1;         6,096,918; 6,218,355 B1; 6,133,228; 6,147,037; 7,109,153 B2;         7,071,151 B2; 6,987,084 B2; 6,610,646 B2 and 5,958,870, as well         as can be found in USPA 2005/0003980 A1 and USPA 2006/0223726         A1.     -   a.) Amine Reaction Product (ARP): For purposes of the present         application, ARP is a subclass or species of PP. One may also         use “reactive” polymeric amines in which the amine functionality         is pre-reacted with one or more PRMs to form an amine reaction         product (ARP). Typically the reactive amines are primary and/or         secondary amines, and may be part of a polymer or a monomer         (non-polymer). Such ARPs may also be mixed with additional PRMs         to provide benefits of polymer-assisted delivery and/or         amine-assisted delivery. Nonlimiting examples of polymeric         amines include polymers based on polyalkylimines, such as         polyethyleneimine (PEI), or polyvinylamine (PVAm). Nonlimiting         examples of monomeric (non-polymeric) amines include         hydroxylamines, such as 2-aminoethanol and its alkyl substituted         derivatives, and aromatic amines such as anthranilates. The ARPs         may be premixed with perfume or added separately in leave-on or         rinse-off applications. In another aspect, a material that         contains a heteroatom other than nitrogen, for example oxygen,         sulfur, phosphorus or selenium, may be used as an alternative to         amine compounds. In yet another aspect, the aforementioned         alternative compounds can be used in combination with amine         compounds. In yet another aspect, a single molecule may comprise         an amine moiety and one or more of the alternative heteroatom         moieties, for example, thiols, phosphines and selenols. The         benefit may include improved delivery of perfume as well as         controlled perfume release. Suitable ARPs as well as methods of         making same can be found in USPA 2005/0003980 A1 and U.S. Pat.         No. 6,413,920 B1.

In one aspect, the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use in perfume delivery systems at levels, based on total perfume delivery system weight, of from 0.001% to about 50%, from 0.005% to 30%, from 0.01% to about 10%, from 0.025% to about 5%, or even from 0.025% to about 1%.

In one aspect, the perfume delivery systems disclosed herein are suitable for use in consumer products, cleaning and treatment compositions and fabric and hard surface cleaning and/or treatment compositions, detergents, and highly compacted consumer products, including highly compacted fabric and hard surface cleaning and/or treatment compositions, for example highly compacted detergents that may be solids or fluids, at levels, based on total consumer product weight, from about 0.001% to about 20%, from about 0.01% to about 10%, from about 0.05% to about 5%, from about 0.1% to about 0.5%.

In one aspect, the amount of Table 1 PRMs, based on the total microcapsules and/or nanocapsules (Polymer Assisted Delivery (PAD) Reservoir System) weight, may be from about 0.1% to about 99%, from 25% to about 95%, from 30 to about 90%, from 45% to about 90%, from 65% to about 90%. In one aspect, microcapsules and/or nanocapsules that may comprise one or more PRMs selected from Table 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161; stereoisomers of Table 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160, 161; and mixtures thereof. PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 21, 22, 23, 24, 25, 26, 27, 30, 31, 32, 33, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 64, 65, 66, 67, 68, 69, 70, 71, 72, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 92, 93, 94, 95, 96, 97, 98, 99, 100, 102, 103, 104, 105, 107, 108, 110, 111, 112, 113, 114, 115, 117, 120, 122, 123, 125, 126, 127, 128, 131, 133, 134, 137, 140, 142, 144, 145, 146, 147, 149, 150, 151, 153, 154, 155, 156, 159 and 160 are ketones. PRMs 15, 16, 17, 18, 19, 20, 116, 118, 119, 129, 135 and 141 are alcohols. PRMs 28, 29 and 52 are esters. PRMs 34, 73, 74, 75, 76, 77, 91, 101, 106, 109, 121, 124, 130, 132, 136, 138, 139, 143, 148, 152, 157, 158 and 161 are nitriles.

In one aspect, the amount of total perfume based on total weight of starch encapsulates and starch agglomerates (Starch Encapsulated Accord (SEA)) ranges from 0.1% to about 99%, from 25% to about 95%, from 30 to about 90%, from 45% to about 90%, from 65% to about 90%. In one aspect, the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use in such starch encapsulates and starch agglomerates. Such PRMs and stereoisomers thereof may be used in combination in such starch encapsulates and starch agglomerates.

In one aspect, the amount of total perfume based on total weight of [cyclodextrin-perfume] complexes (Cyclodextrin (CD)) ranges from 0.1% to about 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% to about 50%, from 5% to about 25%. In one aspect, the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use in such [cyclodextrin-perfume] complexes. Such PRMs and stereoisomers thereof may be used in combination in such [cyclodextrin-perfume] complexes.

In one aspect, the amount of total perfume based on total weight of Polymer Assisted Delivery (PAD) Matrix Systems (including Silicones) ranges from 0.1% to about 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% to about 50%, from 5% to about 25%. In one aspect, the amount of total perfume based on total weight of a hot melt perfume delivery system/perfume loaded plastic Matrix System and ranges from 1% to about 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% to about 50%, from 10% to about 50%. In one aspect, the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use in such Polymer Assisted Delivery (PAD) Matrix Systems, including hot melt perfume delivery system/perfume loaded plastic Matrix Systems. Such PRMs and stereoisomers thereof may be used in combination in such Polymer Assisted Delivery (PAD) Matrix Systems (including hot melt perfume delivery system/perfume loaded plastic Matrix Systems).

In one aspect, the amount of total perfume based on total weight of Amine Assisted Delivery (AAD) (including Aminosilicones) ranges from 1% to about 99%, from 2.5% to about 75%, from 5% to about 60%, from 5% to about 50%, from 5% to about 25%. In one aspect, the PRMs disclosed in Table 1 and stereoisomers thereof are suitable for use in such Amine Assisted Delivery (AAD) systems. Such PRMs and stereoisomers thereof may be used in combination in such Amine Assisted Delivery (AAD) systems. In one aspect, an Amine Assisted Delivery (AAD) system that may comprise one or more PRMs selected from Table 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160 and 161; stereoisomers of Table 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, 99, 100, 101, 102, 103, 104, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 154, 155, 156, 157, 158, 159, 160 and 161; and mixtures thereof is disclosed. PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 21, 22, 23, 24, 25, 26, 27, 30, 31, 32, 33, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 64, 65, 66, 67, 68, 69, 70, 71, 72, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 92, 93, 94, 95, 96, 97, 98, 99, 100, 102, 103, 104, 105, 107, 108, 110, 111, 112, 113, 114, 115, 117, 120, 122, 123, 125, 126, 127, 128, 131, 133, 134, 137, 140, 142, 144, 145, 146, 147, 149, 150, 151, 153, 154, 155, 156, 159 and 160 are ketones. PRMs 15, 16, 17, 18, 19, 20, 116, 118, 119, 129, 135 and 141 are alcohols. PRMs 34, 73, 74, 75, 76, 77, 91, 101, 106, 109, 121, 124, 130, 132, 136, 138, 139, 143, 148, 152, 157, 158 and 161 are nitriles.

In one aspect, a Pro-Perfume (PP) Amine Reaction Product (ARP) system that may comprise one or more PRMs selected from Table 1 PRMs 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 21, 22, 23, 24, 25, 26, 27, 30, 31, 32, 33, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 64, 65, 66, 67, 68, 69, 70, 71, 72, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 92, 93, 94, 95, 96, 97, 98, 99, 100, 102, 103, 104, 105, 107, 108, 110, 111, 112, 113, 114, 115, 117, 120, 122, 123, 125, 126, 127, 128, 131, 133, 134, 137, 140, 142, 144, 145, 146, 147, 149, 150, 151, 153, 154, 155, 156, 159 and 160 is disclosed. Such PRMs are ketones. In one aspect, the amount of total perfume based on total weight of Pro-Perfume (PP) Amine Reaction Product (ARP) system ranges from 0.1% to about 99%, from about 1% to about 99%, from 5% to about 90%, from 10% to about 75%, from 20% to about 75%, from 25% to about 60%.

The perfume delivery technologies also known as perfume delivery systems that are disclosed in the present specification may be used in any combination in any type of consumer product, cleaning and/or treatment composition, fabric and hard surface cleaning and/or treatment composition, detergent, and highly compact detergent.

Perfumes

The PRMs disclosed in Table 1 may be used to formulate perfumes. Such perfumes are combinations of PRMs that may comprise a combination of Table 1 PRMs, or one or Table 1 PRMs and one or more additional PRMs. When used in a perfume, the Table 1 PRMs may used, based on total perfume weight, at levels of from about 0.01% to about 50%, from about 0.1% to about 15%, from about 0.1% to about 10% or even from about 0.5% to about 10%. Such perfumes may be used in multiple applications including being applied neat to a situs or used in a consumer product, cleaning and/or treatment composition, fabric and hard surface cleaning and/or treatment composition, detergent, and/or a highly compact detergent.

Adjunct Materials

For the purposes of the present invention, the non-limiting list of adjuncts illustrated hereinafter are suitable for use in the instant compositions and may be desirably incorporated in certain embodiments of the invention, for example to assist or enhance performance, for treatment of the substrate to be cleaned, or to modify the aesthetics of the composition as is the case with perfumes, colorants, dyes or the like. It is understood that such adjuncts are in addition to the components that are supplied via Applicants' perfumes and/or perfume systems. The precise nature of these additional components, and levels of incorporation thereof, will depend on the physical form of the composition and the nature of the operation for which it is to be used. Suitable adjunct materials include, but are not limited to, surfactants, builders, chelating agents, dye transfer inhibiting agents, dispersants, enzymes, and enzyme stabilizers, catalytic materials, bleach activators, polymeric dispersing agents, clay soil removal/anti-redeposition agents, brighteners, suds suppressors, dyes, additional perfume and perfume delivery systems, structure elasticizing agents, fabric softeners, carriers, hydrotropes, processing aids and/or pigments. In addition to the disclosure below, suitable examples of such other adjuncts and levels of use are found in U.S. Pat. Nos. 5,576,282, 6,306,812 B1 and 6,326,348 B1 that are incorporated by reference.

Each adjunct ingredient is not essential to Applicants' compositions. Thus, certain embodiments of Applicants' compositions do not contain one or more of the following adjuncts materials: bleach activators, surfactants, builders, chelating agents, dye transfer inhibiting agents, dispersants, enzymes, and enzyme stabilizers, catalytic metal complexes, polymeric dispersing agents, clay and soil removal/anti-redeposition agents, brighteners, suds suppressors, dyes, additional perfumes and perfume delivery systems, structure elasticizing agents, fabric softeners, carriers, hydrotropes, processing aids and/or pigments. However, when one or more adjuncts are present, such one or more adjuncts may be present as detailed below:

Surfactants—The compositions according to the present invention can comprise a surfactant or surfactant system wherein the surfactant can be selected from nonionic and/or anionic and/or cationic surfactants and/or ampholytic and/or zwitterionic and/or semi-polar nonionic surfactants. The surfactant is typically present at a level of from about 0.1%, from about 1%, or even from about 5% by weight of the cleaning compositions to about 99.9%, to about 80%, to about 35%, or even to about 30% by weight of the cleaning compositions.

Builders—The compositions of the present invention can comprise one or more detergent builders or builder systems. When present, the compositions will typically comprise at least about 1% builder, or from about 5% or 10% to about 80%, 50%, or even 30% by weight, of said builder. Builders include, but are not limited to, the alkali metal, ammonium and alkanolammonium salts of polyphosphates, alkali metal silicates, alkaline earth and alkali metal carbonates, aluminosilicate builders polycarboxylate compounds. ether hydroxypolycarboxylates, copolymers of maleic anhydride with ethylene or vinyl methyl ether, 1,3,5-trihydroxybenzene-2,4,6-trisulphonic acid, and carboxymethyl-oxysuccinic acid, the various alkali metal, ammonium and substituted ammonium salts of polyacetic acids such as ethylenediamine tetraacetic acid and nitrilotriacetic acid, as well as polycarboxylates such as mellitic acid, succinic acid, oxydisuccinic acid, polymaleic acid, benzene 1,3,5-tricarboxylic acid, carboxymethyloxysuccinic acid, and soluble salts thereof.

Chelating Agents—The compositions herein may also optionally contain one or more copper, iron and/or manganese chelating agents. If utilized, chelating agents will generally comprise from about 0.1% by weight of the compositions herein to about 15%, or even from about 3.0% to about 15% by weight of the compositions herein.

Dye Transfer Inhibiting Agents—The compositions of the present invention may also include one or more dye transfer inhibiting agents. Suitable polymeric dye transfer inhibiting agents include, but are not limited to, polyvinylpyrrolidone polymers, polyamine N-oxide polymers, copolymers of N-vinylpyrrolidone and N-vinylimidazole, polyvinyloxazolidones and polyvinylimidazoles or mixtures thereof. When present in the compositions herein, the dye transfer inhibiting agents are present at levels from about 0.0001%, from about 0.01%, from about 0.05% by weight of the cleaning compositions to about 10%, about 2%, or even about 1% by weight of the cleaning compositions.

Dispersants—The compositions of the present invention can also contain dispersants. Suitable water-soluble organic materials are the homo- or co-polymeric acids or their salts, in which the polycarboxylic acid may comprise at least two carboxyl radicals separated from each other by not more than two carbon atoms.

Enzymes—The compositions can comprise one or more detergent enzymes which provide cleaning performance and/or fabric care benefits. Examples of suitable enzymes include, but are not limited to, hemicellulases, peroxidases, proteases, cellulases, xylanases, lipases, phospholipases, esterases, cutinases, pectinases, keratanases, reductases, oxidases, phenoloxidases, lipoxygenases, ligninases, pullulanases, tannases, pentosanases, malanases, β-glucanases, arabinosidases, hyaluronidase, chondroitinase, laccase, and amylases, or mixtures thereof. A typical combination is a cocktail of conventional applicable enzymes like protease, lipase, cutinase and/or cellulase in conjunction with amylase.

Enzyme Stabilizers—Enzymes for use in compositions, for example, detergents can be stabilized by various techniques. The enzymes employed herein can be stabilized by the presence of water-soluble sources of calcium and/or magnesium ions in the finished compositions that provide such ions to the enzymes.

Catalytic Metal Complexes—Applicants' compositions may include catalytic metal complexes. One type of metal-containing bleach catalyst is a catalyst system comprising a transition metal cation of defined bleach catalytic activity, such as copper, iron, titanium, ruthenium, tungsten, molybdenum, or manganese cations, an auxiliary metal cation having little or no bleach catalytic activity, such as zinc or aluminum cations, and a sequestrate having defined stability constants for the catalytic and auxiliary metal cations, particularly ethylenediaminetetraacetic acid, ethylenediaminetetra(methyl-enephosphonic acid) and water-soluble salts thereof. Such catalysts are disclosed in U.S. Pat. No. 4,430,243.

If desired, the compositions herein can be catalyzed by means of a manganese compound. Such compounds and levels of use are well known in the art and include, for example, the manganese-based catalysts disclosed in U.S. Pat. No. 5,576,282.

Cobalt bleach catalysts useful herein are known, and are described, for example, in U.S. Pat. Nos. 5,597,936 and 5,595,967. Such cobalt catalysts are readily prepared by known procedures, such as taught for example in U.S. Pat. Nos. 5,597,936, and 5,595,967.

Compositions herein may also suitably include a transition metal complex of a macropolycyclic rigid ligand—abbreviated as “MRL”. As a practical matter, and not by way of limitation, the compositions and cleaning processes herein can be adjusted to provide on the order of at least one part per hundred million of the benefit agent MRL species in the aqueous washing medium, and may provide from about 0.005 ppm to about 25 ppm, from about 0.05 ppm to about 10 ppm, or even from about 0.1 ppm to about 5 ppm, of the MRL in the wash liquor.

Suitable transition—metals in the instant transition-metal bleach catalyst include manganese, iron and chromium. Suitable MRL's herein are a special type of ultra-rigid ligand that is cross-bridged such as 5,12-diethyl-1,5,8,12-tetraazabicyclo[6.6.2]hexa-decane.

Suitable transition metal MRLs are readily prepared by known procedures, such as taught for example in WO 00/32601, and U.S. Pat. No. 6,225,464.

Method of Use

Certain of the consumer products disclosed herein can be used to clean or treat a situs inter alia a surface or fabric. Typically at least a portion of the situs is contacted with an embodiment of Applicants' composition, in neat form or diluted in a liquor, for example, a wash liquor and then the situs may be optionally washed and/or rinsed. In one aspect, a situs is optionally washed and/or rinsed, contacted with a particle according to the present invention or composition comprising said particle and then optionally washed and/or rinsed. For purposes of the present invention, washing includes but is not limited to, scrubbing, and mechanical agitation. The fabric may comprise most any fabric capable of being laundered or treated in normal consumer use conditions. Liquors that may comprise the disclosed compositions may have a pH of from about 3 to about 11.5. Such compositions are typically employed at concentrations of from about 500 ppm to about 15,000 ppm in solution. When the wash solvent is water, the water temperature typically ranges from about 5° C. to about 90° C. and, when the situs comprises a fabric, the water to fabric ratio is typically from about 1:1 to about 30:1.

EXAMPLES

While particular embodiments of the present invention have been illustrated and described, it would be obvious to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the invention. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this invention.

Example 1 Synthesis Examples for Table 1 PRMs 1-48

Procedure for the Synthesis of Table 1 Molecule No. 31 (Exemplified for a 7.5 mmolar Scale:

In an oven dried flask were mixed under dry conditions 7.5 mmol of but-3-en-2-ol (1 equiv), 7.5 mmol of sodium methoxide (1 equiv), 9.0 mmol of tributylamine (1.2 equiv), 7.5 mmol of 1-iodo-4-methylbenzene (1 equiv) with 0.75 mmol of PdCl₂ (0.1 equiv) at room temperature in 10 mL of dry DMF. The reaction mixture was stirred while the temperature was first heated to 75° C. for 3 h and for 1 h to 20° C. This temperature cycle was repeated two more times. Then, the reaction mixture was filtered over a short silica path. The silica was washed with methyl tert-butyl ether (MTBE; 2*3 mL). The combined organic fractions were mixed with 25 mL of 0.5 M HCl and extracted with MTBE (2*5 mL) and washed with saturated aqueous NaHCO₃ (5 mL) and brine (5 mL). The crude oil was obtained after drying over MgSO₄, filtration and concentration. Additional flash chromatography was performed to obtain the compound in high purity, with a Biotage PS1: TLC-based method calculated from solvent conditions 80:20-mixture petroleum ether/Ethyl Acetate.

Procedure for the Synthesis of Compound Table 1 Molecule No. 48:

Step 1, Exemplified for a 30 mmolar Scale:

In an oven dried flask were mixed under dry conditions and under nitrogen atmosphere, 30 mmol of the aldehyde (3.6 g) with 1 mL of dry tetrahydrofuran (THF) at room temperature. The reaction mixture was stirred for 10 minutes in an ice bath, before 1.1 equivalents of iso-propylmagnesium chloride, dissolved in THF (2 M; 16.5 mL), were added drop wise upon this solution. The reaction was stirred for 16 h, while the temperature was allowed to come to room temperature. Then, the reaction was quenched by adding it to 17 mL of 2 M HCl, cooled with ice cubes. 30 mL of methyl tert-butyl ether (MTBE) were added to this mixture and was extracted with MTBE (2*10 mL). The combined organic fractions were washed with aqueous saturated NaHCO₃ (5 mL) and brine (5 mL). The crude oil was obtained after drying over MgSO₄, filtration and concentration. The pure compound was obtained after flash chromatography, performed with a Biotage PS1: TLC-based method calculated from solvent conditions 9:1-mixture petroleum ether/Ethyl Acetate.

Step 2, Exemplified for a 24 mmolar Scale:

In an oven dried flask were mixed 24 mmol of the alcohol (5.3 g) with 30 mL of dichloromethane at room temperature. The reaction mixture was stirred for 10 minutes in an ice bath, before 1.1 equivalents of Dess-Martin periodinane (15 w % in CH₂Cl₂; 75 g), were added drop wise upon this solution. The reaction was stirred for 4 days, while the reaction temperature was allowed to come to room temperature. The reaction mixture was quenched by adding it to 100 mL of 1N NaOH solution, cooled with ice cubes. The organic layer was extracted with diethyl ether (Et₂O; 2*15 mL) and washed with aq. NaHCO₃ (10 mL) and brine (10 mL). The crude oil was obtained after drying over MgSO₄, filtration and concentration. Then, the crude oil was dissolved again in Et₂O and kept in the freezer for 16 hours. The white precipitate was filtered of and the filtrate was concentrated. The pure compound was obtained after flash chromatography, performed with a Biotage PS1: TLC-based method calculated from solvent conditions 9:1-mixture petroleum ether/Ethyl Acetate.

Synthesis of Compounds Table 1 Molecules Numbers 2, 3 and 4:

A representative procedure is given for the synthesis of Table 1 Material No. 2 by alkylation of benzyl iso-propyl ketone with bromobutane at the benzylic position:

In a flask were mixed 1.6 mmol of 3-methyl-1-phenylbutan-2-one (1 equiv), 1.9 mmol of n-butylbromide (1.2 equiv), 0.022 mmol of N-benzyltriethylammonium bromide (2 mol %) with 0.5 mL of 50% NaOH at room temperature. The reaction mixture was vigorously stirred at room temperature for 1 h. The temperature of the reaction was increased to 60° C., whilst stirring was continued for 5 h. Then, the reaction mixture was quenched by adding it to a cooled 1 M HCl solution. 10 mL of methyl tert-butyl ether (MTBE) was added and the combined organic fractions were extracted with MTBE (2*5 mL) and washed with saturated aqueous NaHCO₃ (5 mL) and brine (5 mL). The crude oil was obtained after drying over MgSO₄, filtration and concentration. The pure compound was obtained after flash chromatography, performed with a Biotage PS1: TLC-based method calculated from solvent conditions 98:2-mixture petroleum ether/Ethyl Acetate.

Modification of the representative protocol for the analogues is given in the following Table:

Table 1 Reaction time at Molecules No. R¹Br Scale 60° C. 2¹ n-BuBr 1.6 mmol  5 h 3¹ i-PrBr 1.5 mmol 24 h 4¹ EtBr   3 mmol 16 h ¹Flash Chromatography was performed with a Biotage PS1: TLC-based method calculated from solvent conditions 98:2-mixture petroleum ether/Ethyl Acetate.

Synthesis of Table Molecules Numbers: 15, 16, 17, 18, 19 and 20:

A representative procedure is given for the synthesis of Table 1 Molecule No. 16 by addition of ethylmagnesium bromide (R²=Et; X═Br) upon 3-(4-methylcyclohex-3-enyl)butanal (Limonenaldehyde; R¹═H):

A 2-necked 4-L flask was dried for 24 h at 20 mbar and 80° C. in the oven. The glassware was allowed to cool to ambient temperature under nitrogen atmosphere, before 140 gram of 3-(4-methylcyclohex-3-enyl)butanal (Limonenaldehyde; 1 equiv; 0.85 mol) was dissolved in 2.8 L (5 w %) of dry 2-methyltetrahydrofuran (2-MeTHF) under dry conditions (canula). The solution was cooled to −50° C. for 1 hour. Then, 280 mL of ethyl-magnesium bromide, dissolved in 2-MeTHF (3.2 M; 1.06 equiv), were added via a dry dropping funnel under nitrogen atmosphere (over approximately 45 minutes; the temperature of the reaction mixture was probed and not allowed to heat over −40° C.). The reaction was prolonged for 1 hour at −50° C. Then, the reaction was allowed to stir overnight at 0° C. The reaction was quenched by adding it to 1 liter of 1 M HCl, cooled with ice cubes (approx. 600 gram of ice). Then, the aqueous phase was extracted with 2-MeTHF (2*200 mL). The combined organic phases were washed with aqueous sat. bicarbonate (2*100 mL) and with brine (2*100 mL). The combined fractions were dried over MgSO₄, filtered and concentrated at the rotavap. The pure compound was obtained after distillation (111-127° C., 5-10 mbar).

Modification of the representative protocol for the analogues is given in following Table:

Table 1 Carbonyl Reaction Molecule compound Grignard temp (° C.) Purification No. (scale) R², X time [h] protocol 15 Limonenaldehyde R² = Me 0° C., 1 h Biotage¹ (50 mmol) X = Br rt, 16 h 17 4-(4-methyl- R² = Me 0° C., 1 h Biotage¹ cyclohex-3- X = Br rt, 16 h enyl)pentan-2-ol (2 mmol) 16 Limonenaldehyde R² = Et −50° C., 2 h Dist (0.85 mol) X = Br 0° C., 16 h (111-127° C., 5-10 mbar) 19 Limonenaldehyde R² = i-Pr 0° C., 1 h Biotage¹ (20 mmol) X = Cl rt, 16 h 18 Limonenaldehyde R² = Allyl 0° C., 1 h Biotage¹ (10 mmol) X = Cl rt, 16 h 20 Limonenaldehyde R² = t-Eu 0° C., 1 h Biotage¹ (2 mmol) X = Cl rt, 16 h ¹Flash Chromatography was performed with a Biotage PS1: TLC-based method calculated from solvent conditions 85:15-mixture petroleum ether/Ethyl Acetate.

Synthesis of Table 1 Molecules Numbers 21, 22, 23, 24, 25, 26, and 27:

A representative procedure is given for the synthesis of Table 1 Molecule 22 by addition of Dess-Martin periodinane upon 5-(4-methylcyclohex-3-enyl)hexan-3-ol (R¹=Me):

In an oven dried flask were mixed 5.5 gram of 5-(4-methylcyclohex-3-enyl)hexan-3-ol (1 equiv; 30 mmol) with 30 mL of dichloromethane at room temperature. The reaction mixture was stirred for 10 minutes at 0° C., before 1.1 equivalents of Dess-Martin periodinane (15 w % in CH₂Cl₂; 94 g), were added drop wise to this solution. The reaction was stirred for 3 days, while the reaction temperature was allowed to come to room temperature. The reaction mixture was quenched by adding it to 100 mL of 1 N NaOH solution, cooled with ice cubes. The organic layer was extracted with diethyl ether (Et₂O; 2*15 mL) and washed with aqueous saturated NaHCO₃ (10 mL) and brine (10 mL). The crude oil was obtained after drying over MgSO₄, filtration and concentration. Then, the crude oil was dissolved again in Et₂O and kept in the freezer for 16 hours. The white precipitate was filtered of and the filtrate was concentrated at the rotavap. The pure compound was obtained after flash chromatography, performed with a Biotage PS1: TLC-based method calculated from solvent conditions 85:15-mixture petroleum ether/Ethyl Acetate.

Modification of the representative protocol for the analogues is given in the following Table:

Table 1 Alcohol Reaction Molecule No. R¹ = Scale time [h] 22 Me 15 mmol 0° C. rt, 72 h 23 Et 10 mmol 0° C. rt, 16 h 24 i-Pr 10 mmol 0° C. rt, 72 h 26 Allyl 20 mmol 0° C. rt, 16 h 25 n-Pr  1 mmol 0° C. rt, 16 h 21 n-Am  1 mmol 0° C. rt, 16 h 27 t-Bu 20 mmol 0° C. rt, 48 h ¹Flash Chromatography was performed with a Biotage PS1: TLC-based method calculated from solvent conditions 85:15-mixture petroleum ether/Ethyl Acetate.

Synthesis of Table 1 Molecules Numbers 28 and 29:

A representative procedure is given for the synthesis of Table 1 Molecule 29 by acetylation of 5-(4-methylcyclohex-3-enyl)hexan-3-ol:

In an oven dried flask were mixed at room temperature and under helium atmosphere 15 mL of 2-methyltetrahydrofuran (2-MeTHF), 0.15 gram of 4-(dimethylamino)pyridine (DMAP; 0.08 equiv), 8.2 gram of N-methylmorpholine (NMM; 5.3 equiv; 8.9 mL) and 3 gram of 5-(4-methylcyclohex-3-enyl)hexan-3-ol (15 mmol; 1 equiv) under dry conditions. The reaction mixture was stirred for 10 minutes in an ice bath, before 7.8 gram of acetic anhydride (5 equiv; 7.17 mL) was added via a dropping funnel over a 10 minutes period. The reaction was prolonged for 1 hour at 0° C. Then the ice bath was removed and the reaction was continued for 1 h at room temperature while the conversion of the reaction was followed by GC-FID, via analysis of aliquots of the reaction mixture, which were removed by syringe. Then 30 mL of water was added and the reaction mixture was heated to 50° C. for 15 min and extraction was performed at this temperature (2-MeTHF; 2*10 mL). The organic fractions were washed with sat. bi-carbonate and brine, dried over MgSO₄, filtered and concentrated at the rotavap. Additional flash chromatography was performed to obtain the compound in high purity, with a Biotage PS1: TLC-based method calculated from solvent conditions 85:15-mixture petroleum ether/Ethyl Acetate.

Synthesis of Table 1 Molecules Numbers 1, 5, 6, 8, 9, 10, 11, 12, 13 and 14:

A representative procedure is given for the synthesis of Table 1 Molecule 10 by addition of 2-cyclopentylacetyl chloride to benzene:

A 2-L flask, dropping funnel, stiffing bar and septum were dried in the oven at 80° C. and 20 mbar for 24 h. The glassware was cooled to room temperature under nitrogen atmosphere, before 152 gram of aluminium trichloride (AlCl₃; 1.2 equiv) was dissolved in 300 mL of anhydrous benzene. Then, 140 gram of cyclopentylacetyl chloride (1 equiv) were added drop wise and very slowly over a 2 h period to this reaction mixture while the temperature was controlled below 40° C. by the rate of addition of the acid chloride. The reaction start and progress were followed by the gas evolvement. Then, the reaction mixture was continued at 45° C. for 16 h. The reaction mixture was quenched by adding it to a large quantity of crushed ice (1.5 kg). 1 Liter of demineralised water was added, while controlling the temperature with ice. A white suspension was formed. The glassware was washed with 100 mL of methyl tert-butyl ether (MTBE) and the combined organic layers were filtered and extracted with MTBE (2*100 mL). Then the organic layers were washed with aqueous NaHCO₃ solution and brine. The organic fractions were collected, dried over Na₂SO₄, filtered and dried in vacuo (70° C. at 15 mbar) to afford a red oil. This oil was mixed with 10 w % of active carbon and stirred at room temperature for 16 h. Then the mixture was filtered over a short Celite path and the glassware and filter were rinsed with 100 mL of ligroin. The organic fractions were combined and dried at the rotavap, affording a yellow oil.

Modification of the representative protocol for the analogues is given in the following Table:

Table 1 Reaction Purifica- Molecule Acid Chloride temp (° C.) tion No. (scale) Aryl ring time [h] protocol 1 Cyclohexylacetyl benzene rt, 24 h — chloride (30 mmol) 5 Cyclohexylacetyl toluene rt, 4 h — chloride (10 mmol) 6 Cycloheptylacetyl benzene rt, 24 h — chloride (5 mol) 10 Cyclopentylacetyl benzene rt — chloride 45° C., 16 h (500 mmol) 11 3-cyclohexyl- benzene rt Recryst propanoyl chloride 45° C., 16 h (Et₂O) (50 mmol) 12 3-cyclohexyl- ethylbenzene rt, 72 h Biotage¹ propanoyl chloride (50 mmol) 13 3-cyclohexyl- toluene rt, 72 h Recryst propanoyl chloride (Et₂O) (50 mmol) 14 3-cyclohexyl- mesitylene rt, 72 h Biotage¹ propanoyl chloride (30 mmol) 8 Cyclopentylacetyl ethylbenzene 0° C. Biotage¹ chloride rt, 16 h (15 mmol) 9 Cyclopentylacetyl mesitylene 0° C. Biotage¹ chloride rt, 16 h (15 mmol) ¹Flash Chromatography was performed with a Biotage PS1: TLC-based method calculated from solvent conditions 95:5-mixture petroleum ether/Ethyl Acetate.

Synthesis of Table 1 Molecules Numbers 30, 33, 34, 37, 38, 39, 40 and 44:

A representative procedure is given for the synthesis of Table 1 Molecule 33 with para-Tolualdehyde (R¹, R², R⁴═H; R³=Me) and methyl ethyl ketone (R⁵=Me):

In a reaction flask were mixed at room temperature 10.61 mol of ketone (1.7 equiv), 6.24 mol of aldehyde (1 equiv) and 0.5 mol % of RuCl₃.nH₂O (9.2 gram). Then, the reaction mixture was stirred whilst the temperature of the oil bath was increased to 115-130° C. Aliquots of the reaction mixture were removed by syringe and analyzed by GC-FID. Based on the GC-results, the reaction was allowed to progress (in this specific case) until 85% of the starting material was converted over a period of 7 days. Then, the reaction mixture was cooled to room temperature before 1.5 L of toluene was added. The organic phase was extracted with aqueous saturated bicarbonate (4*750 mL). Each time, the aqueous phase was washed with toluene (2*100 mL). After this washing, all the organic phases were combined and washed once more with aqueous saturated bicarbonate (750 mL) and with brine (3*250 mL).

Then, a series of bisulfite washings were performed on the crude oil obtained after concentration of the organic phase at the rotavap (70° C. at 100 mbar). The crude oil was dissolved in equal amounts of toluene and mixed at room temperature with a 40 w % of aqueous NaHSO₃ (1.5 equiv of sodium bisulfite as calculated for the amount of aldehyde present in the crude oil). This mixture was vigorously stirred for 1 hour at room temperature before the organic fraction was decanted. The aqueous layer was extracted once with 50 mL of toluene.

The combined organic fractions were washed with aqueous saturated bicarbonate (2*25 mL) and brine (2*25 mL), dried over MgSO₄, filtered and concentrated. The bisulfite washings were repeated until the total amount of aldehyde was below 4% (in this specific case, three washings were performed). The compound was purified via distillation (4-7 mbar; oil bath 115-160° C.) and recrystallisation from methyl tert-butyl ether (MTBE; 2*200 w %).

Modification of the representative protocol for the analogues is given in the following Table:

Table 1 Mole- Ketone Reaction cule Aldehyde R⁵ temp (° C.) Purification No. R¹,R²,R³,R⁴ (equiv) time [d] protocol 30 R¹,R²,R³,R⁴ = H R⁵ = Me (120) [1] Biotage¹ (0.5 equiv) 33 R¹,R²,R⁴ = H R⁵ = Me (120) [7] Distillation, R³ = Me (1.7 equiv) recrystal- lisation 34 R¹,R²,R⁴ = H R⁵ = Me (120) [7] Biotage¹ R³ = CN (1 equiv) 37 R²,R³,R⁴ = H R⁵ = Me (120) [14] Biotage¹, R¹ = Me (2 equiv)² Dist (102-121° C.; 3-13 mbar) 38 R¹,R³,R⁴ = H R⁵ = Me (125) [1] Biotage¹ R² = Me (0.5 equiv) 39 R¹,R²,R⁴ = H R⁵ = Me (125) [1] Biotage¹ R³ = OMe (0.5 equiv) 40 R¹,R²,R⁴ = H R⁵ = Et (130) [4] Biotage¹, R³ = Me (0.5 equiv) Dist (110-135° C.; 3-5 mbar) 44 R¹,R³,R⁴ = Me R⁵ = Me (125) [7] Dist R² = H (2 equiv)² (91-93° C.; 0.1-0.4 mbar) ¹Flash Chromatography was performed with a Biotage PS1: TLC-based method calculated from solvent conditions 9:1-mixture petroleum ether/Ethyl Acetate. ²more RuCl₃ catalyst was added.

Synthesis of Table 1 Molecules Numbers 32, 35, 36, 41, 42, 43, 45, 46 and 47:

A representative procedure is given for the synthesis of Table 1 Molecule 35 by condensation of benzaldehyde (R¹, R², R³, R⁴═H) with 2-pentanone (R⁵=Et; R⁶, R⁷═H):¹ ¹ In analogy to: Cao, Y.-Q.; Dai, Z.; Zhang, R. and Chen, B.-H. Synth. Commun., 2005, 35, 1045-1049.

In a 2-L flask, 330 gram of benzaldehyde (1 equiv) was mixed with 1 Liter of 2-pentanone (3 equiv). The reaction mixture was cooled to 5-10° C. and thoroughly stirred, before 40 mL of NaOH, 50 w % solution in water (0.5 equiv, 61 g), was slowly added in one portion. After 30 minutes, the temperature of the reaction mixture was allowed to rise to 20° C. The reaction was continued for 5 hours at ambient temperature. Then, the reaction was quenched by adding the reaction mixture to a 2 M HCl solution which was cooled with equal amounts of ice. After extraction with 2-pentanone (2*100 mL), the combined organic fractions were washed with saturated, aqueous bicarbonate solution (50 mL) and brine (50 mL). The organic fractions were combined and concentrated at the rotavap, resulting in a yellow oil. This crude oil was poured in an Erlenmeyer, containing 400 mL of diethyl ether (Et₂O). The flask was rinsed with 100 mL of Et₂O, which was added to the organic phase. Then, 500 mL of aqueous saturated NaHSO₃ solution was added to the combined organic fractions at room temperature. This mixture was vigorously stirred for 1 hour before the organic phase was decanted and washed with saturated, aqueous bicarbonate solution (25 mL) and brine (25 mL). The yellow oil obtained was concentrated at the rotavap and dried at the membrane pump (70° C. at 4 mbar). The compound was first purified via distillation (115-125° C., 1-3 mbar). Afterwards, two additional bisulfite washings were performed.

Modification of the representative protocol for the analogues is given in the following Table:

Com- pound Aldehyde Ketone Purification Number R¹,R²,R³,R⁴ R⁵ equiv ketone protocol 32 R¹,R³,R⁴ = H R⁵ = Me 2.8 equiv Biotage¹ R² = Me R⁶,R⁷ = H 36 R²,R³,R⁴ = H R⁵ = Me 2.8 equiv Biotage¹ R¹ = Me R⁶,R⁷ = H 35 R¹,R²,R³,R⁴ = H R⁵ = Et 3 equiv Dist R⁶,R⁷ = H (115-125° C.; 1-3 mbar) 47 R¹,R³,R⁴ = H R⁵ = Et 3.5 equiv Biotage¹ R² = Me R⁶,R⁷ = H 43 R¹,R³,R⁴ = Me R⁵ = Et 3 equiv Dist R² = H R⁶,R⁷ = H (105-125° C.; 0.1-0.4 mbar) recryst (MTBE) 41 R²,R³,R⁴ = H R⁵ = Et 3.5 equiv Dist R¹ = Me R⁶,R⁷ = H (90-95° C.; 0.01-0.04 mbar) 42 R¹,R³,R⁴ = Me R⁵ = Et 3 equiv Dist R² = H R⁶,R⁷ = H (91-93° C.; 0.1-0.4 mbar) 45 R²,R³ = H R⁵ = Et 3 equiv Dist R¹,R⁴ = Me R⁶,R⁷ = H (105-125° C.; 0.05-0.2 mbar) 46 R²,R³ = H R⁵ = Me 6 equiv Dist R¹,R⁴ = Me R⁶,R⁷ = H (80-90° C.; 0.02-0.1 mbar) ¹Flash Chromatography was performed with a Biotage PS1: TLC-based method calculated from solvent conditions 7:3-mixture petroleum ether/Ethyl Acetate.

Synthesis of Table 1 Molecule Number 7:

Reaction Components 1 Cyclopentylacetyl C₇H₁₁OCl 1 equiv.-10 g Chloride 146.61 g/mol 2 Toluene C₇H₉ 30 mL 92.11 g/mol 3 Aluminium AlCl₃ 1.2 equiv.-10.9 g Chloride 133.34 g/mol

Glassware for parallel synthesis (flask, condenser and dropping funnel), stirring bar, septum and syringe were dried in the oven at 80° C. and 20 mbar for 24 h. All the glassware was mounted as foreseen and was cooled down to room temperature under Argon atmosphere, before AlCl₃ was dissolved in the toluene. The reaction vessel was placed in an ice bath and the acid chloride was added drop wise after some time. Even though the acid chloride was added very slow via the dropping funnel a slightly exothermic reaction started and a lot of gas evolved. Every 2 minutes the pressure was released. The reaction mixture was stirred at room temperature overnight, before the reaction was checked via GC MS. Then the reaction mixture was quenched in demineralised water with 5 ice cubes in it. A white suspension was formed (exothermic; additional ice cubes were added). The glassware was washed with 25 mL of Et₂O and the combined organic layers were filtered and extracted with ether (2*20 mL). Then the organic layers were treated with 2*25 mL of aqueous NaHCO₃ solution and this aqueous layer was extracted again with diethyl ether (2*10 mL). Then, the organic fractions were collected, dried over Na₂SO₄, filtered and dried in vacuum (low pressure; high temperature resulting in a dark oil formed. The compound was placed in the fridge and solidified after some time. It was tried to purify the ketone via re-crystallisation. First it was dissolved in the minimal amount of Et₂O. Upon cooling it solidified after a few hours. This procedure was repeated two times resulting in colourless crystals.

Synthesis of Table 1 Molecule Number 49, 50 & 61:

applied Compound scale (mmol Number R substrate) 49 t-Bu 10 50 i-Pr 11 61 Me 10

A representative procedure is given for the synthesis of Table 1 Molecule 50.

Step 1.

A solution of n-butyllithium (2.2M in cyclohexane—1 eq.) was added drop wise to an ice cold solution of diisopropylamine (1 eq.) in dry THF. After stirring for 10 minutes at this temperature, propionitrile (5 eq.) was added to the mixture. Prenyl bromide (1 eq.) was added after another mixing of 10 minutes at 0° C. Reaction conversion was followed by GC-MS and seen as complete after 15 minutes stirring at 0° C.

The reaction was quenched by addition of saturated NH₄Cl aqueous solution and extracted with Et₂O. The combined organic layers were dried over MgSO₄ and concentrated under reduced pressure. The resulting oil was purified using a quick filtration over silica by elution with a petroleum ether—Et₂O mixture (9-1). Concentration of the eluent under reduced pressure resulted in the compound as a colorless oil.

Step 2.

A methyllithium solution (1.2 equiv.) was added drop wise to a solution of the nitrile (1 eq.) in dry THF (0.5M) at −20° C. After stiffing for 15 minutes at −10/−20° C., full conversion was observed by GC-MS. The reaction was quenched with a H₂SO₄ solution (2M—2 eq.) and stirred at ambient temperature till full hydrolysis of the in situ formed imine was observed. The mixture was then extracted with Et₂O and washed with a saturated NaHCO₃ aqueous solution. The combined organic phases were dried over MgSO₄ and concentrated under reduced pressure. The resulting oil was purified with column chromatography by eluting with a petroleum ether—MTBE mixture (95-5). Concentration of the desired fractions under reduced pressure resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 52:

Compound 52 was synthesized starting from 20 mmol 4,4-dimethyl-3-oxopentanoate.

Step 1.

To a solution of 4,4-dimethyl-3-oxopentanoate (1 eq.) and K₂CO₃ (2.2 eq.) in dry acetone (0.9 M) was added iodomethane (3.3 eq.) at 60° C. The mixture was stirred for 16 hours at the same temperature and dried over MgSO₄ after cooling to ambient temperature. The organic mixture was concentrated under reduced pressure to yield the product without further purification.

Step 2.

The β-keto-ester (1 eq.) formed in step 1 was solved in MTBE (0.6 M) and sodium t-butoxide (1.1 eq.) and prenyl bromide (1.5 eq.) were added at room temperature. The resulting mixture was stirred for 16 hours at the same temperature and quenched with an aqueous H₂SO₄ solution (0.5 M). After extracting the mixture with MTBE, the collected organic layers were dried over MgSO₄ and concentrated under reduced pressure. The resulting oil was purified by column chromatography using a petroleum ether—MTBE mixture (95-5) as eluens. Concentration of the eluent under reduced pressure resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 53:

Compound 53 was synthesized starting from 45 mmol 3,3-dimethyl-2-butanone.

A solution of n-butyllithium (2.2M in cyclohexane—2 eq.) was added drop wise to an ice cold solution of diisopropylamine (2 eq.) in dry THF (0.5 M). After stiffing for 10 minutes at this temperature, 3,3-dimethyl-2-butanone (1 eq.) was added to the mixture. Prenyl bromide (2 eq.) was added after another mixing of 10 minutes at 0° C. Reaction conversion was followed by GC-MS and seen as complete after 12 h at ambient temperature.

The reaction was quenched by addition of saturated NH₄Cl aqueous solution and extracted with Et₂O. The combined organic layers were dried over MgSO₄ and concentrated under reduced pressure. The resulting oil was purified by column chromatography using a petroleum ether-MTBE mixture (95-5) as eluens. Concentration of the eluent under reduced pressure resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 63:

Compound 63 was synthesized starting from 15 mmol lavandulol.

To a stirred solution of lavandulol (1 eq.) in dry CH₂Cl₂ (0.2 M) at ambient temperature was added NaHCO₃ (4 eq.) and Dess-Martin periodane (1.5 eq.). Complete reaction conversion was observed via GC-MS after 1 hour stiffing at the same temperature. The reaction was quenched by the addition of petroleum ether and filtered over a silica gel plug and rinsed with a petroleum ether—Et₂O mixture (9-1). The crude aldehyde is obtained by concentration under reduced pressure.

This aldehyde was resolved in t-BuOH (0.2 M) and 2-methyl-2-butene (0.6 M). The resulting solution was cooled to 0° C. and a solution of NaClO₂ (10 eq.) and NaH₂PO₄ (8 eq.) in water (0.3 M) was added. The reaction mixture was allowed to warm to ambient temperature and stirred for 2 hours. The resulting mixture was quenched by the addition of a phosphate buffer (pH 7). The two layers were separated and the aqueous layer was extracted with CH₂Cl₂. The combined organic phases were dried over MgSO₄ and concentrated under reduced pressure. Column chromatography using the eluent petroleum ether—Et₂O (1-1) resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 73, 74, 75, 76, 77, 91, 106, 109, 121, 124, 130, 132, 136, 138, 139, 143, 148, 152, 157, 158 & 161:

applied scale Compound (mmol Number R¹ R² substrate) 73 R¹ = Me, H

28

74 2R¹ = cyclopentyl

54 75 2R¹ = cyclohexyl

64 76 2R¹ = cyclopropyl

63 77 2R¹ = cyclobutyl

600 91 Me

165 106 Me

137 109 2R¹ = cyclopropyl

68 121 Me

72 124 Me

55 130 Me

28 132 2R¹ = cyclobutyl

49 136 2R¹ = cyclopropyl

54

A representative procedure is given for the synthesis of Table 1 Molecule 152.

A solution of n-butyllithium (2.2M in cyclohexane—1 eq.) was added drop wise to an ice cold solution of diisopropylamine (1 eq.) in dry THF (0.5 M). After stirring for 10 minutes at this temperature, i-butyronitrile (1 eq.) was added to the mixture. 3-Bromocyclohex-1-ene (1 eq.) was added after another mixing of 10 minutes at 0° C. Reaction conversion was followed by GC-MS and seen as complete after 15 minutes stirring at 0° C.

The reaction was quenched by addition of a saturated NH₄Cl aqueous solution and extracted with Et₂O. The combined organic layers were dried over MgSO₄ and concentrated under reduced pressure. The resulting oil was purified using a quick filtration over silica by elution with a petroleum ether—Et₂O mixture (9-1). Concentration of the eluent under reduced pressure resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 51, 54, 55, 56, 57, 58, 59, 60, 62, 64, 65, 66, 67, 68, 69, 70, 71, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 92, 93, 94, 95, 96, 97, 98, 99, 100, 102, 103, 104, 107, 108, 110, 111, 112, 113, 114, 115, 117, 122, 126, 127, 128, 131, 133, 134, 137, 142, 149, 150, 151, 153, 154, 155, 156, 159 & 160:

Compound applied scale Number Nitrile R³ (mmol substrate) 51 91 t-Bu 6 54 75 Me 5 55 75 Et 6 14 56 75 i-Pr Compound 62 was isolated as side product in the imine hydrolysis to compound 56. 57 91 Et 16 58 74 Me 12 59 74 Et 12 60 73 Me 8 64 74 i-Pr 15 65 73 Et 10 66 73 i-Pr 10 67 91 s-Bu 15 68 76 Me 7 69 76 s-Bu 15 70 76 i-Pr 15 71 76 n-Bu 15 78 77 s-Bu 11 79 77 Me 13 80 [935-44-4] s-Bu 10 81 77 n-Bu 11 82 77 i-Pr 13 83 [935-44-4] Et 14 84 [935-44-4] i-Pr 13 85 76 Et 14 86 76 i-Bu 13 87 [71172-78-6] Et 11 88 [71172-78-6] s-Bu 10 89 [15760-35-7] Me 10 90 [14377-68-5] n-Bu 10 92 91 n-Bu 11 93 91 i-Bu 11 94 74 n-Bu 10 95 74 i-Bu 10 96 76 t-Bu 12 97 [71172-78-6] i-Pr 11 98 described in Me 9 nitrile synthesis 99 protocol s-Bu 8 100 101 i-Pr 11 102 101 Me 12 103 101 Et 13 104 [68983-70-0] Me 11 107 106 Me 12 108 106 Et 12 110 106 s-Bu 129 111 109 Et 11 112 109 Me 11 113 109 s-Bu 10 114 109 i-Pr 11 115 [35863-45-7] i-Bu 10 117 77 Et 167 122 121 Et 10 126 124 s-Bu 9 127 121 Me 10 128 124 Et 10 131 130 i-Pr 10 133 132 Me 11 134 132 i-Pr 19 137 136 Me 12 142 139 Me 9 149 148 Et 9 150 148 n-Bu 9 151 143 Me 12 153 152 i-Bu 11 154 143 n-Bu 9 155 152 Et 12 156 143 Et 10 159 158 n-Bu 11 160 157 Me 11

A representative procedure is given for the synthesis of Table 1 Molecule 151.

A methyllithium solution (1.2 equiv.) was added drop wise to a solution of the nitrile (1 eq.) in dry THF (0.5M) at −20° C. After stiffing for 15 minutes at −10/−20° C., full conversion was observed by GC-MS.

The reaction was quenched with a H₂SO₄ solution (2M—2 eq.) and stirred at ambient temperature till full hydrolysis of the in situ formed imine was observed. The mixture was then extracted with Et₂O and washed with a saturated NaHCO₃ aqueous solution. The combined organic phases were dried over MgSO₄ and concentrated under reduced pressure. The resulting oil was purified using a quick filtration over silica gel by eluting with a petroleum ether—Et₂O mixture (9-1). Concentration of the eluent under reduced pressure resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 72, 105, 120, 123, 144, 145, 146 & 147:

Compound applied scale Number RM (mmol substrate) 72 EtMgBr 146 105 PhLi 7 120 VinylMgBr 100 123 cyclopentylMgCl 5 144 n-BuLi 6 145 i-PrMgCl 6 146 i-BuLi 6 147 t-BuLi 5

A representative procedure is given for the synthesis of Table 1 Molecule 72.

Step 1.

To a solution of the phosphonium bromide [50889-29-7] (1.2 eq.) in dry THF (0.3 M) was added KHMDS (Potassiumhexamethyldisilazane—2.4 eq.) at ambient temperature. After stirring for 30 minutes at the same temperature, a solution of acetone (1 eq.) in dry THF (0.3 M) was added drop wise. The mixture was stirred for 3 hours, quenched with water (0.3 M) and extracted with Et₂O. The resulting water layer was acidified with a HCl aqueous solution (10%) till pH 2 was obtained. This mixture was extracted with Et₂O and the extracts were dried over MgSO₄ and concentrated under reduced pressure. The resulting oil was purified using a quick filtration over silica gel by eluting with a petroleum ether—Et₂O mixture (1-1). Concentration under reduced pressure resulted in the compound as a slightly yellow oil.

Step 2.

To a solution of the acid formed in step 1 (1 eq.) in dry CH₂Cl₂ (0.5 M) was added 1,1′-carbonyldiimidazole (1 eq.) at ambient temperature. The mixture was stirred for 15 minutes and N,O-Dimethylhydroxylamine hydrochloride (1 eq.) was added. Stirring was continued at the same temperature for 1 hour and the mixture was quenched with an aqueous HCl solution (1 M—1.1 eq.). The aqueous layer was extracted with Et₂O, washed with NaHCO₃ and dried over MgSO₄. Concentration under reduced pressure resulted in the compound as a colorless oil.

Step 3.

The Weinreb amide formed in step 2 was solved in dry THF (0.5 M) and cooled to −15° C. A solution of EtMgBr (1 M—1.5 eq.) was added drop wise to the mixture. Complete reaction conversion was observed with GC-MS after 10 minutes stirring at −10/−15° C. This reaction mixture was quenched with a saturated aqueous NH₄Cl solution, extracted with Et₂O; dried over MgSO₄ and concentrated under reduced pressure. The resulting oil was purified using a quick filtration over silica gel by eluting with a petroleum ether—Et₂O mixture (9-1). Concentration under reduced pressure resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 101:

Compound 101 was synthesized starting from 100 mmol nitrile [2947-60-6].

To a solution of diisopropylamine (2.2 eq.—28.1 mL) in dry THF (0.5 M) was added drop wise a solution of n-butyllithium (2.2 eq.—100 mL 2.2 M) at 0° C. 2-m-Tolylacetonitrile (1 eq.—13 mL) was added to the solution after 10 minutes of stirring at the same temperature. A supplementary stirring for 10 minutes was followed by the drop wise addition of iodomethane (2.5 eq.—15.6 mL). Reaction completion was observed after 10 minutes stirring at 0° C. The mixture was quenched with an aqueous solution of NH₄Cl, extracted with Et₂O, dried over MgSO₄ and concentrated under reduced pressure. The resulting oil was purified using a quick filtration over silica gel by eluting with a petroleum ether—Et₂O mixture (9-1). Concentration under reduced pressure resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 116, 118 & 129:

Compound applied scale Number R¹ R² R³ R⁴ (mmol substrate) 116 2R¹ = cyclopropyl prenyl Me Me 13 118 2R¹ = cyclobutyl prenyl Et Me 8 129 2R¹ = cyclobutyl prenyl Et n-Bu 10

A representative procedure is given for the synthesis of Table 1 Molecule 116.

To a solution of compound 68 (1 eq.) in dry THF (0.5 M) was added a solution of methylmagnesium bromide (1.5 eq.—3M) at −20° C. The reaction mixture was allowed to warm to ambient temperature and stiffing was continued for 2 hours. The reaction was quenched with the addition of a saturated aqueous NH₄Cl solution and extracted with Et₂O. The combined organic layers were dried over MgSO₄ and concentrated under reduced pressure. The resulting oil was purified by column chromatography using the eluens petroleum ether—MTBE (95-5). Concentration of the required fractions resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 119, 135 & 141:

applied scale Compound (mmol Number Ketone R¹ R² R³ substrate) 119 117 2R¹ = prenyl Et 8 cyclobutyl 135 134 2R¹ = cyclobutyl

i-Pr 7 141 140 2R¹ = cyclopropyl

allyl 11

A representative procedure is given for the synthesis of Table 1 Molecule 119.

To a solution of compound 117 (1 eq.) in dry Et₂O (0.5 M) was added portion wise lithium-aluminiumhydride (1 eq.) at 0° C. Reaction completion was observed by GC-MS after 15 minutes of stirring at ambient temperature. The mixture was cooled to 0° C. and consequently was added: water (same amount of mL as mg hydride used), 15% NaOH solution (same amount of mL as mg hydride used) & water (2 times amount of mL as mg hydride used). This quenching was followed by stirring for 1 hour at ambient temperature. The resulting mixture was filtered over celite and the filter was washed with Et₂O. Concentration of the filtrate under reduced pressure resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 125:

Compound 125 was synthesized starting from 11 mmol iso-butyronitrile.

Step 1.

4-Fluoro-2-methylanisole (1 eq.) was solved in dry THF (0.7 M) and KHMDS (Potassiumhexa-methyldisilazane—1.5 eq.) was added at room temperature. The mixture was heated to 60° C. after the addition of iso-butyronitrile (4 eq.). Refluxing was continued for 12 hours. The reaction was quenched with an aqueous HCl solution (1M) and extracted with Et₂O. The organic layers were dried over MgSO₄ and concentrated under reduced pressure (1 mbar at 55° C.). The resulting oil was purified using a quick filtration over silica gel by eluting with a petroleum ether—Et₂O mixture (9-1). Concentration under reduced pressure resulted in the compound as a colorless oil.

Step 2.

The nitrile formed in step 1 was solved in dry THF (0.5 M) and cooled to −20° C. A solution of methyllithium (1.3 eq.—1.6 M) was added drop wise. Reaction completion was observed after 10 minutes stiffing at −20° C. The reaction was quenched with a H₂SO₄ solution (2M—2 eq.) and stirred at ambient temperature till full hydrolysis of the in situ formed imine was observed (over night ambient temperature). The mixture was then extracted with Et₂O and washed with a saturated NaHCO₃ aqueous solution. The combined organic phases were dried over MgSO₄ and concentrated under reduced pressure. The resulting oil was purified using a quick filtration over silica gel by eluting with a petroleum ether—Et₂O mixture (9-1). Concentration of the eluent under reduced pressure resulted in the compound as a colorless oil.

Synthesis of Table 1 Molecule Number 140:

Compound 140 was synthesized starting from 24 mmol acid [6120-95-2].

Step 1.

To a solution of 1-Phenyl-1-cyclopropanecarboxylic acid (1 eq.) in dry CH₂Cl₂ (0.5 M) was added 1,1′-carbonyldiimidazole (1 eq.) at ambient temperature. The mixture was stirred for 15 minutes and N,O-dimethylhydroxylamine hydrochloride (1 eq.) was added. Stirring was continued at the same temperature for 1 hour and the mixture was quenched with an aqueous HCl solution (1 M—1.1 eq.). The aqueous layer was extracted with Et₂O, washed with NaHCO₃ and dried over MgSO₄. Concentration under reduced pressure resulted in the compound as a colorless oil.

Step 2.

The Weinreb amide formed in step 2 was solved in dry THF (0.5 M) and cooled to −15° C. A solution of EtMgBr (1 M—1.5 eq.) was added drop wise to the mixture. Complete reaction conversion was observed with GC-MS after 10 minutes stirring at −10/−15° C. This reaction mixture was quenched with a saturated aqueous NH₄Cl solution, extracted with Et₂O; dried over MgSO₄ and concentrated under reduced pressure. The resulting oil was purified using a quick filtration over silica gel by eluting with a petroleum ether—Et₂O mixture (9-1). Concentration under reduced pressure resulted in the compound as a colorless oil.

Example 2 Preformed Amine Reaction Product

The following ingredients are weighted off in a glass vial:

50% of the perfume material comprising one or more Table 1 PRMs

50% of Lupasol WF (CAS #09002-98-6) from BASF, is put at 60° C. in warm water bath for 1 hour before use. Mixing of the two ingredients was done by using the Ultra-Turrax T25 Basic equipment (from IKA) during 5 minutes. When the mixing is finished the sample is put in a warm water bath at 60° C. for ±12 hours. A homogenous, viscous material is obtained.

In the same way as described above different ratios between the components can be used:

Weight % Perfume Material 40 50 60 70 80 Lupasol WF 60 50 40 30 20

Example 3 84 wt % Core/16 wt % Wall Melamine Formaldehyde (MF) Capsule (PAD Reservoir System

25 grams of butyl acrylate-acrylic acid copolymer emulsifier (Colloid C351, 25% solids, pka 4.5-4.7, (Kemira Chemicals, Inc. Kennesaw, Ga. U.S.A.) is dissolved and mixed in 200 grams deionized water. The pH of the solution is adjusted to pH of 4.0 with sodium hydroxide solution. 8 grams of partially methylated methylol melamine resin (Cymel 385, 80% solids, (Cytec Industries West Paterson, N.J., U.S.A.)) is added to the emulsifier solution. 200 grams of perfume oil comprising one or more Table 1 PRMs is added to the previous mixture under mechanical agitation and the temperature is raised to 50° C. After mixing at higher speed until a stable emulsion is obtained, the second solution and 4 grams of sodium sulfate salt are added to the emulsion. This second solution contains 10 grams of butyl acrylate-acrylic acid copolymer emulsifier (Colloid C351, 25% solids, pka 4.5-4.7, Kemira), 120 grams of distilled water, sodium hydroxide solution to adjust pH to 4.8, 25 grams of partially methylated methylol melamine resin (Cymel 385, 80% solids, Cytec). This mixture is heated to 70° C. and maintained overnight with continuous stirring to complete the encapsulation process. 23 grams of acetoacetamide (Sigma-Aldrich, Saint Louis, Mo., U.S.A.) is added to the suspension. An average capsule size of 30 μm is obtained as analyzed by a Model 780 Accusizer.

Example 4 Process of Making a Polymer Assisted Delivery (PAD) Matrix System

A mixture comprising 50% of a perfume composition comprising one or more Table 1 PRMs, 40% of carboxyl-terminated Hycar®1300×18 (CAS #0068891-50-9) from Noveon, (put at 60° C. in warm water bath for 1 hour before mixing) and 10% of Lupasol® WF (CAS #09002-98-6) from BASF (put at 60° C. in warm water bath for 1 hour before mixing). Mixing is achieved by mixing for five minutes using a Ultra-Turrax T25 Basic equipment (from IKA). After mixing, the mixture is put in a warm water bath at 60° C. for ±12 hours. A homogenous, viscous and sticky material is obtained.

In the same way as described above different ratios between the components can be used:

Weight % Perfume composition 40 50 60 70 80 Lupasol ® WF 12 10 8 6 4 Hycar ® 48 40 32 24 16 CTBN1300X18

Weight % Perfume composition 50 50 50 50 50 50 50 50 Lupasol ® WF 2.5 5 7.5 10 12.5 15 17.5 20 Hycar ® 47.5 45 42.5 40 37.5 35 32.5 30 CTBN 1300X18

Example 5 Product Formulation

Non-limiting examples of product formulations containing PRMs disclosed in the present specification perfume and amines summarized in the following table.

EXAMPLES (% wt) XI XII XIII XIV XV XVI XVII XVIII XIX XX FSA ^(a) 14 16.47 14 12 12 16.47 — — 5 5 FSA ^(b) — 3.00 — — — FSA ^(c) — — 6.5 — — Ethanol 2.18 2.57 2.18 1.95 1.95 2.57 — — 0.81 0.81 Isopropyl — — — — — — 0.33  1.22 — — Alcohol Starch ^(d) 1.25 1.47 2.00 1.25 — 2.30 0.5  0.70 0.71 0.42 Amine * 0.6 0.75 0.6 0.75 0.37 0.60 0.37 0.6 0.37 0.37 Perfume X ^(e) 0.40 0.13 0.065 0.25 0.03 0.030 0.030  0.065 0.03 0.03 Phase 0.21 0.25 0.21 0.21 0.14 — —  0.14 — — Stabilizing Polymer ^(f) Suds — — — — — — — 0.1 — — Suppressor ^(g) Calcium 0.15 0.176 0.15 0.15 0.30 0.176 — 0.1-0.15 — — Chloride DTPA ^(h) 0.017 0.017 0.017 0.017 0.007 0.007 0.20 — 0.002 0.002 Preservative 5 5 5 5 5 5 — 250 ^(j)   5 5 (ppm) ^(i, j) Antifoam ^(k) 0.015 0.018 0.015 0.015 0.015 0.015 — — 0.015 0.015 Dye (ppm) 40 40 40 40 40 40 11 30-300 30 30 Ammonium 0.100 0.118 0.100 0.100 0.115 0.115 — — — — Chloride HCl 0.012 0.014 0.012 0.012 0.028 0.028 0.016  0.025 0.011 0.011 Structurant ^(l) 0.01 0.01 0.01 0.01 0.01 0.01 0.01  0.01 0.01 0.01 Additional 0.8 0.7 0.9 0.5 1.2 0.5 1.1 0.6 1.0 0.9 Neat Perfume Deionized † † † † † † † † † † Water ^(a) N,N-di(tallowoyloxyethyl)-N,N-dimethylammonium chloride. ^(b) Methyl bis(tallow amidoethyl)2-hydroxyethyl ammonium methyl sulfate. ^(c) Reaction product of Fatty acid with Methyldiethanolamine in a molar ratio 1.5:1, quaternized with Methylchloride, resulting in a 1:1 molar mixture of N,N-bis(stearoyl-oxy-ethyl) N,N-dimethyl ammonium chloride and N-(stearoyl-oxy-ethyl) N,-hydroxyethyl N,N dimethyl ammonium chloride. ^(d) Cationic high amylose maize starch available from National Starch under the trade name CATO ®. ^(e) Perfume comprising one or more Table 1 PRMs. ^(f) Copolymer of ethylene oxide and terephthalate having the formula described in U.S. Pat. No. 5,574,179 at col. 15, lines 1-5, wherein each X is methyl, each n is 40, u is 4, each R1 is essentially 1,4-phenylene moieties, each R2 is essentially ethylene, 1,2-propylene moieties, or mixtures thereof. ^(g) SE39 from Wacker ^(h) Diethylenetriaminepentaacetic acid. ^(i) KATHON ® CG available from Rohm and Haas Co. “PPM” is “parts per million.” ^(j) Gluteraldehyde ^(k) Silicone antifoam agent available from Dow Corning Corp. under the trade name DC2310. ^(l) Hydrophobically-modified ethoxylated urethane available from Rohm and Haas under the tradename Aculan 44. * One or more materials comprising an amine moiety as disclosed in the present specification. † balance

Example 6 Dry Laundry Formulations

% w/w granular laundry detergent composition Component A B C D E F G Brightener 0.1 0.1 0.1 0.2 0.1 0.2 0.1 Soap 0.6 0.6 0.6 0.6 0.6 0.6 0.6 Ethylenediamine disuccinic acid 0.1 0.1 0.1 0.1 0.1 0.1 0.1 Acrylate/maleate copolymer 1.5 1.5 1.5 1.5 1.5 1.5 1.5 Hydroxyethane di(methylene 0.4 0.4 0.4 0.4 0.4 0.4 0.4 phosphonic acid) Mono-C₁₂₋₁₄ alkyl, di-methyl, 0.5 0.5 0.5 0.5 0.5 0.5 0.5 mono-hydroyethyl quaternary ammonium chloride Linear alkyl benzene 0.1 0.1 0.2 0.1 0.1 0.2 0.1 Linear alkyl benzene sulphonate 10.3 10.1 19.9 14.7 10.3 17 10.5 Magnesium sulphate 0.4 0.4 0.4 0.4 0.4 0.4 0.4 Sodium carbonate 19.5 19.2 10.1 18.5 29.9 10.1 16.8 Sodium sulphate 29.6 29.8 38.8 15.1 24.4 19.7 19.1 Sodium Chloride 0.1 0.1 0.1 0.1 0.1 0.1 0.1 Zeolite 9.6 9.4 8.1 18 10 13.2 17.3 Photobleach particle 0.1 0.1 0.2 0.1 0.2 0.1 0.2 Blue and red carbonate speckles 1.8 1.8 1.8 1.8 1.8 1.8 1.8 Ethoxylated Alcohol AE7 1 1 1 1 1 1 1 Tetraacetyl ethylene diamine 0.9 0.9 0.9 0.9 0.9 0.9 0.9 agglomerate (92 wt % active) Citric acid 1.4 1.4 1.4 1.4 1.4 1.4 1.4 PDMS/clay agglomerates (9.5% 10.5 10.3 5 15 5.1 7.3 10.2 wt % active PDMS) Polyethylene oxide 0.2 0.2 0.2 0.2 0.2 0.2 0.2 Enzymes e.g. Protease (84 mg/g 0.2 0.3 0.2 0.1 0.2 0.1 0.2 active), Amylase (22 mg/g active) Suds suppressor agglomerate 0.2 0.2 0.2 0.2 0.2 0.2 0.2 (12.4 wt % active) Sodium percarbonate (having 7.2 7.1 4.9 5.4 6.9 19.3 13.1 from 12% to 15% active AvOx) Additional Neat Perfume** 0.5 0.5 0.5 0.5 0.5 0.5 0.5 Amine* 0.1 0.5 0.0 0.01 0.02 0.00 0.07 Perfume Delivery System As 0.05 0.0 0.1 0.0 0.2 0.4 0.0 Disclosed In The Present Specification Including Examples 2-4 Perfume comprising one or more 0.3 0.4 0.01 0.02 0.04 0.1 0.1 PRMs from Table 1 Water 1.4 1.4 1.4 1.4 1.4 1.4 1.4 Misc 0.1 0.1 0.1 0.1 0.1 0.1 0.1 Total Parts 100 100 100 100 100 100 100 *One or more materials comprising an amine moiety as disclosed in the present specification. **Optional

Example 7 Liquid Laundry Formulations (HDLs)

Ingredient HDL 1 HDL 2 HDL3 HDL4 HDL 5 HDL 6 Alkyl Ether Sulphate 0.00 0.50 12.0 12.0 6.0 7.0 Dodecyl Benzene 8.0 8.0 1.0 1.0 2.0 3.0 Sulphonic Acid Ethoxylated Alcohol 8.0 6.0 5.0 7.0 5.0 3.0 Citric Acid 5.0 3.0 3.0 5.0 2.0 3.0 Fatty Acid 3.0 5.0 5.0 3.0 6.0 5.0 Ethoxysulfated 1.9 1.2 1.5 2.0 1.0 1.0 hexamethylene diamine quaternized Diethylene triamine penta 0.3 0.2 0.2 0.3 0.1 0.2 methylene phosphonic acid Enzymes 1.20 0.80 0 1.2 0 0.8 Brightener (disulphonated 0.14 0.09 0 0.14 0.01 0.09 diamino stilbene based FWA) Cationic hydroxyethyl 0 0 0.10 0 0.200 0.30 cellulose Poly(acrylamide-co- 0 0 0 0.50 0.10 0 diallyldimethylammonium chloride) Hydrogenated Castor Oil 0.50 0.44 0.2 0.2 0.3 0.3 Structurant Boric acid 2.4 1.5 1.0 2.4 1.0 1.5 Ethanol 0.50 1.0 2.0 2.0 1.0 1.0 1,2 propanediol 2.0 3.0 1.0 1.0 0.01 0.01 Glutaraldehyde 0 0 19 ppm 0 13 ppm 0 Diethyleneglycol (DEG) 1.6 0 0 0 0 0 2,3-Methyl-1,3- 1.0 1.0 0 0 0 0 propanediol (M pdiol) Mono Ethanol Amine 1.0 0.5 0 0 0 0 NaOH Sufficient To pH 8 pH 8 pH 8 pH 8 pH 8 pH 8 Provide Formulation pH of: Sodium Cumene 2.00 0 0 0 0 0 Sulphonate (NaCS) Silicone (PDMS) emulsion 0.003 0.003 0.003 0.003 0.003 0.003 Additional Neat Perfume** 0.7 0.5 0.8 0.8 0.6 0.6 Amine* 0.01 0.10 0.0 0.10 0.20 0.05 Perfume comprising one or 0.02 0.15 0.0 0.2 0.3 0.1 more PRMs from Table 1 Perfume Delivery System 0.2 0.02 0.4 0.0 0.0 0.0 As Disclosed In The Present Specification Including Examples 2-4 Water Balance Balance Balance Balance Balance Balance *One or more materials comprising an amine moiety as disclosed in the present specification. **Optional.

Example 8 Shampoo Formulation

Ingredient Ammonium Laureth Sulfate (AE₃S) 6.00 Ammonium Lauryl Sulfate (ALS) 10.00  Laureth-4 Alcohol 0.90 Trihydroxystearin ⁽⁷⁾ 0.10 Perfume comprising one or more 0.60 PRMs from Table 1 Sodium Chloride 0.40 Citric Acid 0.04 Sodium Citrate 0.40 Sodium Benzoate 0.25 Ethylene Diamine Tetra Acetic Acid 0.10 Dimethicone ^((9, 10, 11))   1.00 ⁽⁹⁾ Water and Minors (QS to 100%) Balance

Example 9 Fine Fragrance Formulation

Ingredient 1 2 3 Cyclic oligosaccharide 0 5 10 Ethanol 90 75 80 Perfume comprising one or more 10 20 10 PRMs from Table 1

The dimensions and values disclosed herein are not to be understood as being strictly limited to the exact numerical values recited. Instead, unless otherwise specified, each such dimension is intended to mean both the recited value and a functionally equivalent range surrounding that value. For example, a dimension disclosed as “40 mm” is intended to mean “about 40 mm”

All documents cited in the Detailed Description of the Invention are, in relevant part, incorporated herein by reference; the citation of any document is not to be construed as an admission that it is prior art with respect to the present invention. To the extent that any meaning or definition of a term in this document conflicts with any meaning or definition of the same term in a document incorporated by reference, the meaning or definition assigned to that term in this document shall govern.

While particular embodiments of the present invention have been illustrated and described, it would be obvious to those skilled in the art that various other changes and modifications can be made without departing from the spirit and scope of the invention. It is therefore intended to cover in the appended claims all such changes and modifications that are within the scope of this invention. 

1. A perfume raw material comprising 2-(R,S)-(1-(3-methylbut-2-enyl)cyclobutyl)butan-2-ol.
 2. A perfume comprising, based on total perfume weight, from about 0.01% to about 50%, of 2-(R,S)-(1-(3-methylbut-2-enyl)cyclobutyl)butan-2-ol.
 3. A consumer product comprising, based on total consumer product weight, from about 0.0001% to about 25% of 2-(R,S)-(1-(3-methylbut-2-enyl)cyclobutyl)butan-2-ol.
 4. A consumer product according to claim 3, said consumer product being a cleaning and/or treatment composition, said composition comprising, based on total composition weight, from about 0.0001% to about 25% of 2-(R,S)-(1-(3-methylbut-2-enyl)cyclobutyl)butan-2-ol.
 5. A consumer product according to claim 3, said consumer product being a fabric and/or hard surface cleaning and/or treatment composition, said composition comprising, based on total composition weight, from about 0.00001% to about 25% of 2-(R,S)-(1-(3-methylbut-2-enyl)cyclobutyl)butan-2-ol.
 6. A consumer product according to claim 3, said consumer product being a detergent, said detergent comprising, based on total detergent weight, from about 0.00001% to about 25% of 2-(R,S)-(1-(3-methylbut-2-enyl)cyclobutyl)butan-2-ol.
 7. A consumer product according to claim 3, said consumer product being a highly compacted consumer product, said highly compacted consumer product comprising based on total highly compacted consumer product weight, from about 0.00001% to about 25% of 2-(R,S)-(1-(3-methylbut-2-enyl)cyclobutyl)butan-2-ol.
 8. A perfume delivery system comprising from 0.001% to about 50% of 2-(R,S)-(1-(3-methylbut-2-enyl)cyclobutyl)butan-2-ol, said perfume delivery system being a polymer assisted delivery system; molecule-assisted delivery system; fiber-assisted delivery system; amine assisted delivery system; cyclodextrin delivery system; starch encapsulated accord; inorganic carrier delivery system; or pro-perfume.
 9. A perfume delivery system according to claim 8, said perfume delivery system being nanocapsule or microcapsule comprising, based on total nanocapsule or microcapsule weight, from about 0.1% to about 99% of 2-(R,S)-(1-(3-methylbut-2-enyl)cyclobutyl)butan-2-ol. 